78955-90-5|Methyl 4-chloro-2-methoxybenzoate| Ambeed

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Quality Control of [ 78955-90-5 ] Purity: 98% SDS Specification

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Product Details of [ 78955-90-5 ]

CAS No. :	78955-90-5
Formula :	C₉H₉ClO₃
M.W :	200.62
SMILES Code :	O=C(OC)C1=CC=C(Cl)C=C1OC
MDL No. :	MFCD09800922
Boiling Point :	No data available
InChI Key :	UTEXPQWKBMXWJD-UHFFFAOYSA-N
Pubchem ID :	327084

Safety of [ 78955-90-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302+H312+H332-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P363-P403+P233-P405-P501

Application In Synthesis of [ 78955-90-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 78955-90-5 ]

[ 78955-90-5 ] Synthesis Path-Downstream 1~35

1
[ 78955-90-5 ]
[ 57479-70-6 ]

References: [1]Chemische Berichte,1951,vol. 84,p. 557,561.
[2]New Journal of Chemistry,2019,vol. 43,p. 1874 - 1884.

2
[ 5106-98-9 ]
[ 77-78-1 ]
[ 78955-90-5 ]

References: [1]Chemische Berichte,1951,vol. 84,p. 557,561.
[2]New Journal of Chemistry,2019,vol. 43,p. 1874 - 1884.

3
[ 78955-90-5 ]
[ 10308-82-4 ]
5-(4-Chloro-2-methoxy-phenyl)-2H-[1,2,4]triazol-3-ylamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3019 - 3029.

4
[ 78955-90-5 ]
[ 556-61-6 ]
5-amino-3-(4-chloro-2-methoxyphenyl)-1-[methylamino(thiocarbonyl)]-1H-1,2,4-triazole [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3019 - 3029.

5
[ 58621-39-9 ]
[ 78955-90-5 ]
[ 198351-08-5 ]

References: [1]Archiv der Pharmazie,1997,vol. 330,p. 215 - 224.

6
[ 1765-93-1 ]
[ 78955-90-5 ]
4'-fluoro-3-methoxybiphenyl-4-carboxylic acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 656 - 663.

7
[ 78955-90-5 ]
[ 878465-96-4 ]

Yield	Reaction Conditions	Operation in experiment
73%	With hydrazine; In methanol;Heating / reflux;	(b) 4-Chloro-2-methoxybenzohydrazide. A mixture of methyl4-chloro-2-methoxybenzoate (6.0 g, 29.9 mmol), methanol (50 mL) and hydrazine hydrate (6.0 mL, 123.3 mmol) was refluxed overnight. The reaction mixture was cooled to room temperature and the precipitate was collected by filtration and further dried under vacuum to give the title compound as white solids (4.36 g, 21.7 mmol, 73%). 1H NMR (DMSO-d6): 9.24 (broad, s, IH)5 7.65 (d, IH, J = 8.4 Hz)3 7.19 (d, IH3 J = 2.1 Hz)3 7.08 (dd3 IH, J = 1.8, 8.1 Hz), 4.53 (d, 2H3 J= 4.2 Hz), 3.88 (s, 3H).

References: [1]Patent: WO2008/11045,2008,A2 .Location in patent: Page/Page column 107.
[2]Chemistry - An Asian Journal,2010,vol. 5,p. 543 - 549.

8
[ 755027-16-8 ]
[ 78955-90-5 ]
methyl 2-methoxy-4-(11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-3-yl)benzoate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4162 - 4176.

9
[ 5106-98-9 ]
[ 74-88-4 ]
[ 78955-90-5 ]

Yield	Reaction Conditions	Operation in experiment
77.4%	In N-methyl-acetamide;	(1) Methyl 4-chloro-2-methoxybenzoate To a suspension of 60% sodium hydride oil (3.4 g) in dimethylformamide (25 ml) was added 4-chlorosalicylic acid (7.33 g) under ice-cooling, and the mixture was stirred for 1 hour at room temperature. After the stirring, iodomethane (25 g) was dropwise added to the mixture and the mixture was reacted for 1 hour at 50 C., which was followed by extraction with ether. The extract was washed with water and dried over magnesium sulfate. After the concentration, the residue was chromatographed on silica gel (hexane-ethyl acetate) to give 6.60 g of a colorless transparent liquid (yield 77.4%). IR (neat) δ: 2940, 1725, 1595, 1570 cm-1 1 H-NMR (DMSO-d6) δ: 3.79 (3H, s), 3.86 (3H, s), 7.09 (1H, d, J=8.3, 1.8 Hz), 7.25 (1H, d, J=1.8 Hz), 7.68 (1H, d, J=8.3 Hz) (2) 5-Amino-3-(4-chloro-2-methoxyphenyl)-1H-1,2,4-triazole

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6463 - 6466.
[2]Patent: US5750545,1998,A .
[3]Chemistry - An Asian Journal,2010,vol. 5,p. 543 - 549.

10
[ 78955-90-5 ]
[ 90296-27-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 3h;Inert atmosphere;	To a solution under nitrogen gas of methyl 2-methoxy-4-chlorobenzoate (10.0 g, 50 mmol) in THF (100 mL) was added at 0C a 1.0 M LiAlH4 solution in THF (75 mL, 75 mmol). The resulting reaction mixture was stirred at room temperature for 3 hours. Then, the solvent was removed under vacuum and the residue was stirred in a 5% aqueous acetic acid solution (pH 6) for 15 minutes. The aqueous layer was extracted with EtOAc, then the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the crude product as a tan oil. The crude product was purified by flash chromatography (gradient petroleum ether/EtOAc 100/5) to give 7.5 g (yield = 87 %) of white solid corresponding to 2-methoxy-4-chlorobenzyl alcohol (14-1). 1H NMR (400 MHz, CDCl3)
	With lithium borohydride; In tetrahydrofuran; at 60℃; for 16h;Inert atmosphere;	General procedure: To a solution of methyl 4-bromo-2-methoxybenzoate (7.14g, 29mmol) in THF (35mL) was added a 2M solution of LiBH4 in THF (35mL, 70mmol, 2.4equiv). The solution was heated at 60C for 16h. The reaction was then cooled to room temperature, and the solvent was removed under vacuum. The residue was stirred in a 5% aqueous acetic acid solution (pH 6) for 15min. The aqueous layer was extracted with EtOAc (2×50mL), then the combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated to yield the crude product as a tan oil. The oil was purified by flash chromatography using 5% EtOAc in hexanes to provide 5.96g (94%) of the product as a white solid.
	With methanol; sodium tetrahydroborate; at 60℃; for 4h;	Step 2; To the solution of meihyl 4-chioro-2-methoxybenzoate in 5 mL of MeOH was added aBH4 (304 mg, 8.04 mmol). The reaction was stirred at 60 C for 4h. The completion of the reaction was monitored by HPLC. Upon completion, solvent was removed in vacuo, H2O was added to the crude residue and the reaction mixture was extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaHC03, brine and dried over Na2'04. Filtration and removal of the solvent provided 49 mg (35% overall yield) of the title compound as a colorless oil, which was used without further purification; . 1H N (400 MHz, CDC ) ~ 7.22 (d, J - 7.9 Hz, 1 H), 6.94 (dd, J = 2,0, 7.9 Hz, 1 H), 6.88 (d, J ~ 2.0 Hz, 1 H), 4.65 (s, 2 H), 3.87 (s, 3 H).

References: [1]Patent: EP3620164,2020,A1 .Location in patent: Paragraph 1513; 1514.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6463 - 6466.
[3]ChemMedChem,2010,vol. 5,p. 65 - 78.
[4]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 419 - 434.
[5]ChemMedChem,2016,vol. 11,p. 2607 - 2620.
[6]Patent: WO2018/52903,2018,A1 .Location in patent: Page/Page column 68.

11
[ 78955-90-5 ]
6-chloro-benzofuran-3-ol [ No CAS ]

References: [1]Chemische Berichte,1951,vol. 84,p. 557,561.

12
[ 78955-90-5 ]
1,4-bis-(4-chloro-2-methoxy-phenyl)-but-2<i>t</i>-ene-1,4-dione [ No CAS ]

References: [1]Chemische Berichte,1951,vol. 84,p. 557,561.

13
[ 78955-90-5 ]
[ 545436-74-6 ]

References: [1]Chemische Berichte,1951,vol. 84,p. 557,561.

14
[ 78955-90-5 ]
[ 98-80-6 ]
[ 175152-70-2 ]

Yield	Reaction Conditions	Operation in experiment
41.2%	With caesium carbonate;bis-triphenylphosphine-palladium(II) chloride; In DMF (N,N-dimethyl-formamide); at 120℃; for 8h;	Dichlorobis(triphenylphosphine)palladium(29mg, 0.04mmol) was added to a solution of <strong>[78955-90-5]methyl 4-chloro-2-methoxybenzoate</strong>(904mg, 4.5mmol), phenylboronic acid(500mg, 4.1mmol) and cesium carbonate(2.7g, 8.2mmol) in N,N-dimethylformamide(15mL) under argon atmosphere, and the mixture was stirred at 120C for 8 hours. After the reaction mixture was cooled to room temperature, it was diluted with ethyl acetate. The ethyl acetate layer was washed successively with water and brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel(n-hexane:ethyl acetate=10:1) to give the title compound(410mg, 41.2%) as a colourless oil.1H-NMR(CDCl3): δ 3.91(3H, s), 3.98(3H, s), 7.17(1H, d, J=1.5Hz), 7.20(1H, dd, J=8.1, 1.5Hz), 7.31-7.50(3H, m), 7.59-7.63(2H, m), 7.89(1H, d, J=8.1Hz).
41.2%	With caesium carbonate;bis-triphenylphosphine-palladium(II) chloride; In DMF (N,N-dimethyl-formamide); at 120℃; for 8h;	Dichlorobis(triphenylphosphine)palladium(29mg, 0.04mmol) was added to a solution of <strong>[78955-90-5]methyl 4-chloro-2-methoxybenzoate</strong>(904mg, 4.5mmol), phenylboronic acid(500mg, 4.1mmol) and cesium carbonate(2.7g, 8.2mmol) in N,N-dimethylformamide(15mL) under argon atmosphere, and the mixture was stirred at 120C for 8 hours. After the reaction mixture was cooled to room temperature, it was diluted with ethyl acetate. The ethyl acetate layer was washed successively with water and brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel(n-hexane:ethyl acetate=10:1) to give the title compound(410mg, 41.2%) as a colourless oil.1H-NMR(CDCl3): δ 3.91(3H, s), 3.98(3H, s), 7.17(1H, d, J=1.5Hz), 7.20(1H, dd, J=8.1, 1.5Hz), 7.31-7.50(3H, m), 7.59-7.63(2H, m), 7.89(1H, d, J=8.1Hz).
41.2%	With caesium carbonate;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 120℃; for 8h;	(1) Methyl 2-methoxy-4-phenylbenzoate. Dichlorobis(triphenylphosphine)palladium(29mg, 0.04mmol) was added to a solution of <strong>[78955-90-5]methyl 4-chloro-2-methoxybenzoate</strong>(904mg, 4.5mmol), phenylboronic acid(500mg, 4.1mmol) and cesium carbonate(2.7g, 8.2mmol) in N,N-dimethylformamide(15mL) under argon atmosphere, and the mixture was stirred at 120C for 8 hours. After the reaction mixture was cooled to room temperature, it was diluted with ethyl acetate. The ethyl acetate layer was washed successively with water and brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel(n-hexane:ethyl acetate=10:1) to give the title compound(410mg, 41.2%) as a colourless oil. 1H-NMR(CDCl3): δ 3.91(3H, s), 3.98(3H, s), 7.17(1H, d, J=1.5Hz), 7.20(1H, dd, J=8.1, 1.5Hz), 7.31-7.50(3H, m), 7.59-7.63(2H, m), 7.89(1H, d, J=8.1Hz).

References: [1]Patent: EP1535609,2005,A1 .Location in patent: Page/Page column 123-124.
[2]Patent: EP1555018,2005,A1 .Location in patent: Page/Page column 123.
[3]Patent: EP1512396,2005,A1 .Location in patent: Page/Page column 199.

15
[ 78955-90-5 ]
[ 53581-86-5 ]

Yield	Reaction Conditions	Operation in experiment
		(137-3) 4-Chloro-2-methoxybenzaldehyde was obtained from the compound of Example 137-2 in a similar manner to Example 28-4. 1H NMR (CDCl3, 400 MHz) δ 10.39 (s, 1H), 7.77 (d, 1H, J=8.3 Hz), 7.02 (dd, 1H, J=1.7, 8.3 Hz), 6.99 (d, 1H, J=1.7 Hz), 3.94 (s, 3H).
		(137-3) 4-Chloro-2-methoxybenzaldehyde was obtained from the compound of Example 137-2 in a similar manner to Example 28-4. 1H NMR (CDCl3, 400MHz) δ 10.39 (s, 1H), 7.77 (d, 1H, J=8.3Hz), 7.02 (dd, 1H, J=1.7, 8.3Hz), 6.99 (d, 1H, J=1.7Hz), 3.94 (s, 3H).

References: [1]Patent: US2003/181496,2003,A1 .
[2]Patent: EP1479384,2004,A1 .
[3]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 419 - 434.

16
ethyl 3-(4-chloro-2-methoxyphenyl)acrylate [ No CAS ]
[ 78955-90-5 ]

Yield	Reaction Conditions	Operation in experiment
		(137-6) Under nitrogen atmosphere, the title compound was obtained from the compound of Example 137-5 and the compound of Example 109-6 in a similar manner to Example 18-3. 1H NMR (CDCl3, 400 MHz) δ 7.83 (d, 2H, J=8.9 Hz), 7.32 (d, 1H, J=8.2 Hz), 6.94 (d, 2H, J=8.9 Hz), 6.87 (dd, 1H, J=1.9, 8.2 Hz), 6.83 (d, 1H, J=1.3 Hz), 6.82 (d, 1H, J=1.9 Hz), 6.76 (d, 1H, J=16.0 Hz), 6.42 (dt, 1H, J=16.0, 6.4 Hz), 6.21 (d, 1H, J=1.3 Hz), 5.11 (d, 2H, J=6.4 Hz), 3.88 (s, 3H), 3.81 (s, 3H), 2.08 (s, 3H).

References: [1]Patent: US2003/181496,2003,A1 .

17
[ 78955-90-5 ]
[ 94319-98-9 ]

Yield	Reaction Conditions	Operation in experiment
	With ethylenediamine;	In an analogous manner, from 20 g (0.1 mol) of methyl 4-chloro-2 -methoxybenzoate and 20.1 ml (0.3 mol) of ethylenediamine there were obtained 8.9 g of N-(2-aminoethyl) -4-chloro-2-anisamide hydrochloride, m.p. 132-135. (decomposition).

References: [1]Patent: US5238962,1993,A .

18
[ 78955-90-5 ]
[ 925-90-6 ]
[ 902137-24-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	With 4-methyl-morpholine; iron(III) acetylacetonate; In tetrahydrofuran; for 0.25h;	To a solution of <strong>[78955-90-5]methyl 4-chloro-2-methoxybenzoate</strong> (example 18d) (4.16 g, 20.8 mmol) in THF (120 mL) and NMP (12 mL) was added under inert atmosphere Iron(III) acetylacetonate (398 mg, 1.17 mmol) giving a red color. Then EtMgBr (29 ml of 1M solution in ether) was added dropwise under vigorous stirring. The mixture turned dark brown and then violet and then was stirred for 15 more min. The reaction was diluted with ether and quenched upon the addition of aq. HCl (1M, 50 mL). The crude product was extracted with ether and the combined organic layers were successively washed with water and brine, dried over MgSO4, filtered and evaporated. The residue was purified on silica gel (Eluent: 30% EtOAc in hexanes) to give methyl 4-ethyl-2-methoxybenzoate (2.01 g, 50%) as an oil. 1H NMR (300 MHz, dMSO): δ 1.20-1.22(t, 3H), 2.65-2.7 (dd, 2H), 3.9 (s, 3H), 6.8 (s, 1H), 6.97 (m, 1H), 7.7 (m, 1H).

References: [1]Patent: US2006/263411,2006,A1 .Location in patent: Page/Page column 41.

19
[ 67-56-1 ]
[ 57479-70-6 ]
[ 78955-90-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sulfuric acid;Heating / reflux;	(a) Methyl 4-chloro-2-methoxybenzoate. A mixture of 4-chloro-2- methoxybenzoic acid (5.02 g, 6.90 mmol) in 75 mL of methanol and 1 mL of concentrated sulfuric acid was refluxed overnight. The reaction mixture was cooled to room temperature and methanol was removed under vacuum. The residue was dissolved in 200 mL of ethyl acetate and washed with saturated NaHCO3 (150 mL x 2). The organic layer was dried under anhydrous Na2SO4, filtered and concentrated to obtain title product as a clear oil (5.19 g, 6.62 mmol. 96%). 1H NMR (CDCl3): 7.62 (d, IH, J= 8.6 Hz), 7.01 (d, IH, J - 2.4 Hz), 6.98 (dd, IH, J= 1.9, 8.8 Hz), 3.88 (s, 3H).
96%	With sulfuric acid;Heating / reflux;	A suspension of 4-chloro-2-methoxybenzoic acid (5 g, 27 mmol) in MeOH (18 mL) and conc. H2SO4 (1.5 mL) was refluxed overnight. MeOH was evaporated and the residue was extracted to EtOAc and successively washed with water and brine, dried over MgSO4, filtered and evaporated to give methyl 4-chloro-2-methoxybenzoate as a white solid (5.17 g, 96%).
	With sulfuric acid; at 80℃;	Step 1 : To the solution of 4-chloro~2-methoxybenzoic acid (150 mg, 0.80 mmol} in 5 mL of MeOH was added 0.5 mL of H2SO4. The reaction was stirred overnight at 80 C. The compleiion of the reaction was monitored by HPLC. Upon completion, the solvent was removed in vacuo, H.2O was added to the crude residue and the reaction mixture was extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaHCOs, brine and dried over Na20 . Filtration and removal of the solvent in vacuo provided methyl 4~ehoro~2~ (0609) methoxybenzoate, which was used without further purification; 1H NMR (400 MHz, CD.CI3). δ = 7.77 {d, J - 8.8 Hz, 1 H), 7.01 - 6.95 (m, 2 H), 3.92 (s, 3 H), 3.89 (s, 3 H).

References: [1]Patent: WO2008/11045,2008,A2 .Location in patent: Page/Page column 106-107.
[2]Patent: US2006/263411,2006,A1 .Location in patent: Page/Page column 41.
[3]ChemMedChem,2016,vol. 11,p. 2607 - 2620.
[4]Patent: WO2018/52903,2018,A1 .Location in patent: Page/Page column 68.

Yield	Reaction Conditions	Operation in experiment
100%		(137-2) Under nitrogen atmosphere, a solution of the compound of Example 137-1 (4.50 g) in THF (75 mL) was cooled to 0C, and thereto was added LiAlH4 (984 mg) in portions. The mixture was stirred at room temperature for 2 hours, and cooled to 0C. Water (1.0 mL), a 2N aqueous NaOH solution (2.0 mL) and water (1.0 mL) were added successively to the mixture, and the mixture was stirred at room temperature for 1 hour. The solid was collected by filtration, and washed with ethyl acetate. The filtrate and the washing were combined, washed with a saturated brine, and dried over MgSO4. The solvent was evaporated under reduced pressure to give (4-chloro-2-methoxyphenyl)methanol (3.88 g, 100 %). 1H NMR (CDCl3, 400MHz) δ 7.21(d, 1H, J=8.0 Hz), 6.93 (dd, 1H, J=1.9, 8.0 Hz), 6.87 (d, 1H, J=1.9Hz), 4.64 (s, 2H), 3.86 (s, 3H).

21
[ 22717-55-1 ]
[ 74-88-4 ]
[ 78955-90-5 ]