[ CAS No. 65784-33-0 ] {[proInfo.proName]}

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Quality Control of [ 65784-33-0 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 65784-33-0 ]

CAS No. :	65784-33-0	MDL No. :
Formula :	C₁₀H₁₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	180.20	Pubchem ID :	-
Synonyms :

Safety of [ 65784-33-0 ]

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Application In Synthesis of [ 65784-33-0 ]

* 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.

Upstream synthesis route of [ 65784-33-0 ]
Downstream synthetic route of [ 65784-33-0 ]

[ 65784-33-0 ] Synthesis Path-Upstream 1~1

1
[ 67-56-1 ]
[ 2628-16-2 ]
[ 201230-82-2 ]
[ 54965-55-8 ]
[ 5597-50-2 ]
[ 65784-33-0 ]

Reference： [1] Chemical Communications, 2015, vol. 51, # 63, p. 12574 - 12577
[2] Chemical Communications, 2015, vol. 51, # 63, p. 12574 - 12577

[ 65784-33-0 ] Synthesis Path-Downstream 1~11

1
[ 5445-25-0 ]
[ 65784-33-0 ]
[ 77143-73-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium 1) toluene, reflux, 8 h, 2) reflux, 8 h; Multistep reaction;

Reference： [1]Shridhar, D. R.; Sastry, C. V. Reddy; Mehrotra, A. K.; Bansal, O. P. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 10, p. 891 - 893]

2
[ 3199-50-6 ]
[ 65784-33-0 ]
[ 99834-91-0 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 993 - 995

3
[ 89891-83-8 ]
[ 65784-33-0 ]
[ 120569-04-2 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1988,vol. 36,p. 3462 - 3467

4
[ 65784-33-0 ]
[ 120569-07-5 ]
[ 120608-36-8 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1988,vol. 36,p. 3462 - 3467

5
[ 50415-73-1 ]
[ 65784-33-0 ]

Yield	Reaction Conditions	Operation in experiment
32 g	With aluminium trichloride In benzene for 7h; Heating;

Reference： [1]Bell, Vivien L.; Giddings, Peter J.; Holmes, Andrew B.; Mock, Graham A.; Raphael, Ralph A. [Journal of the Chemical Society. Perkin transactions I, 1986, p. 1515 - 1522]

6
[ 65784-33-0 ]
[ 74-88-4 ]
[ 50415-73-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methyl 2-(4-hydroxyphenyl)propanoate With potassium carbonate In acetone at 20℃; for 1h; Stage #2: methyl iodide In acetone at 20℃;

Reference： [1]Allegretti, Marcello; Bertini, Riccardo; Cesta, Maria Candida; Bizzarri, Cinzia; Di Bitondo, Rosa; Di Cioccio, Vito; Galliera, Emanuela; Berdini, Valerio; Topai, Alessandra; Zampella, Giuseppe; Russo, Vincenzo; Di Bello, Nicoletta; Nano, Giuseppe; Nicolini, Luca; Locati, Massimo; Fantucci, Piercarlo; Florio, Saverio; Colotta, Francesco [Journal of Medicinal Chemistry, 2005, vol. 48, # 13, p. 4312 - 4331]

7
[ 65784-33-0 ]
[ 942-54-1 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 4312 - 4331

8
[ 942-54-1 ]
[ 65784-33-0 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1981,vol. 46,p. 1173 - 1187

9
[ 67-56-1 ]
[ 65784-33-0 ]
[ 50415-73-1 ]

Yield	Reaction Conditions	Operation in experiment
81%	With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 6h;	2-(4-Methoxy-phenyl)-propionic acid HVDRAZIDE [0404] Methyl (4-methoxyphenyl)-2-propionate (334 mg, 1.85 mmol) and hydrazine mono- hydrate (0.1 ml, 2.06 mmol) was dissolved in ethanol (4 ML). It was heated to reflux and stirred for 2 days at this temperature. It was concentrated in vacuum, the precipitate was filtered and washed with ethanol. The title compound was obtained as a white solid in quantitative yield. [0405] HNMR (400 MHz, DB-DMSO) 61. 30 (D, J= 7. 0 Hz, 3H), 3.72 (s, 3H), 6. 85 (d, J = 8.6 Hz, 2H), 7.22 (d, J= 8.6 Hz, 2H), 9.11 (s, 1 H). [0406] The propionate was synthesized as follows : [0407] Methyl (4-hydroxyphenyl)-2-propionate (377 mg, 2. 27 MMOL), triphenylphosphine (713 mg, 2. 72 MMOL), diethylazodicarboxylate (0.43 ml, 2.73 mmol and methanol (0.14 ML, 3.5 mmol) were dissolved in tetrahydrofuran (THF) (4 ml) at room temperature. It was stirred for 6 h at room temperature. The solvent was removed and the residue was purified by chromatotron (ethylacetate/hexanes = 3/1). The title compound (356 mg, 81 %) was obtained as A pale yellow oil. [0408] 1H NMR (400 MHz, D6-DMSO) 6 1. 36 (D, J = 7. 0 HZ, 3H), 3. 57 (s, 3H), 3. 73 (s, 3H), 6. 88 (d, J = 9. 0 Hz, 2H), 7. 19 (D, J = 8. 6 Hz, 2H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2005/5378, 2005, A2 Location in patent: Page/Page column 85

10
[ 65784-33-0 ]
[ 288399-19-9 ]
[ 864657-84-1 ]

Yield	Reaction Conditions	Operation in experiment
	With tetra-(n-butyl)ammonium iodide; caesium carbonate; In dimethyl sulfoxide; at 50℃; for 1h;	(ii) To a solution of methyl 2- (4-hydroxyphenyl) propionate (5.0 g, 27.7 mmol) in DMSO (60 ml) was added <strong>[288399-19-9]4-chloromethyl-2-methylquinoline</strong>t (6.33 g, 27.7 mmol), caesium carbonate (9.04 g, 27.7 mmol) and tetra-n-butylammonium iodide (10.25 g, 27.7 mmol). The resultant solution was stirred at 50 C for 60 min. The reaction mixture was allowed to cool then diluted with ethyl acetate (450 ml) and washed with brine (3 x 50 ml). The organic phase was dried (MgSO4), evaporated and purified by chromatography (Companion, 120g silica Redisep column, eluent 0<75% EtOAc/isohexane) to give methyl 2- [4- (2-methyl-quinolin- 4-ylmethoxy)-phenyl] propionate (3.81 g, 11.36 mmol) as an oil. NMR (CDCl3) : 1.45 (d, 3H), 2.70 (s, 3H), 3.60 (s, 3H), 3.65 (m, 1H), 5.45 (s, 2H), 6.95 (d, 2H), 7.20 (d, 2H), 7.40 (s, 1H), 7.45 (t, 1H), 7.65 (t, 1H), 7.85 (d, 1H), 8.00 (d, 1H); MS (M+H) + 336.
	With tetra-(n-butyl)ammonium iodide; caesium carbonate; In dimethyl sulfoxide; at 50℃; for 1h;	(ii) To a solution of methyl 2- (4-hydroxyphenyl) propionate (5.0 g, 27.7 mmol) in DMSO (60 ml) was added <strong>[288399-19-9]4-chloromethyl-2-methylquinoline</strong> (described at the end of Example 1) (6.33 g, 27.7 mmol), caesium carbonate (9.04 g, 27.7 mmol) and tetra-n-butylammonium iodide (10.25 g, 27.7 mmol). The resultant solution was stirred at 50 C for 60 min. The reaction mixture was allowed to cool then diluted with EtOAc (450 ml) and washed with brine (3 x 50 ml). The organic phase was dried (MgS04), evaporated and purified by chromatography (Companion, 120g silica Redisep column, eluent 0<75% EtOAc/ isohexane) to give methyl 2- [4- (2-methyl-quinolin-4-ylmethoxy)-phenyl] propionate (3.81 g, 11.36 mmol) as an oil. NMR (CDCl3) : 1.45 (d, 3H), 2.70 (s, 3H), 3.60 (s, 3H), 3.65 (m, 1H), 5.45 (s, 2H), 6.95 (d, 2H), 7.20 (d, 2H), 7.40 (s, 1H), 7.45 (t, 1H), 7.65 (t, 1H), 7.85 (d, 1H), 8.00 (d, 1H) ; MS (M+H) + 336.
	With tetra-(n-butyl)ammonium iodide; caesium carbonate; In dimethyl sulfoxide; at 50℃; for 1h;	(ii) To a solution of methyl 2- (4-hydroxyphenyl) propionate (5.0 g, 27.7 mmol) in DMSO (60 ml) was added <strong>[288399-19-9]4-chloromethyl-2-methylquinoline</strong> (described at the end of Example 1) (6.33 g, 27.7 mmol), caesium carbonate (9.04 g, 27.7 mmol) and tetra-n-butylammonium iodide (10.25 g, 27.7 mmol). The resultant solution was stirred at 50 C for 60 min. The reaction mixture was allowed to cool then diluted with EtOAc (450 ml) and washed with brine (3 x 50 ml). The organic phase was dried (MgS04), evaporated and purified by chromatography (Companion, 120g silica Redisep column, eluent 0<75% EtOAc/ isohexane) to give methyl 2- [4- (2-methyl-quinolin-4-ylmethoxy)-phenyl] propionate (3.81 g, 11.36 mmol) as an oil. NMR (CDC13) : 1.45 (d, 3H), 2.70 (s, 3H), 3.60 (s, 3H), 3.65 (m, 1H), 5.45 (s, 2H), 6.95 (d, 2H), 7.20 (d, 2H), 7.40 (s, 1H), 7.45 (t, 1H), 7.65 (t, 1H), 7. 85 (d, 1H), 8.00 (d, 1H); MS (M+H) + 336.

	With tetra-(n-butyl)ammonium iodide; caesium carbonate; at 50℃; for 1h;	(ii) To a solution of methyl 2- (4-hydroxyphenyl) propionate (5.0 g, 27.7 mmol) in DMSO (60 ml) was added <strong>[288399-19-9]4-chloromethyl-2-methylquinoline</strong>t (6.33 g, 27.7 mmol), caesium carbonate (9.04 g, 27.7 mmol) and tetra-n-butylammonium iodide (10.25 g, 27.7 mmol). The resultant solution was stirred at 50 C for 60 min. The reaction mixture was allowed to cool then diluted with ethyl acetate (450 ml) and washed with brine (3 x 50 ml). The organic phase was dried (MgS04), evaporated and purified by chromatography (Companion, 120g silica Redisep column, eluent 0--+75% EtOAc/isohexane) to give methyl 2- [4- (2-methylquinolin-4- ylmethoxy) phenyl] propionate (3.81 g, 11. 36 mmol) as an oil. NMR (CDC13) : 1.45 (d, 3H), 2.70 (s, 3H), 3.60 (s, 3H), 3.65 (m, 1H), 5.45 (s, 2H), 6.95 (d, 2H), 7.20 (d, 2H), 7.40 (s, 1H), 7.45 (t, 1H), 7.65 (t, 1H), 7.85 (d, 1H), 8. 00 (d, 1H) ; MS (M+H) + 336.
	With di-tert-butyl (E)-azodicarboxylate; triphenylphosphine; In dichloromethane; at 20℃; for 4h;	(ii) To a solution of <strong>[288399-19-9]4-chloromethyl-2-methylquinoline</strong> (described at the end of Example 1) (1.06g, 6. 2mmol), methyl 2- (4-hydroxyphenyl) propionate (1.0 g, 5.6 mmol), triphenylphosphine (2. 56g, 9. 8mmol) in DCM (15ml), under Ar, di-tert-butyl (E)-diazene-1, 2- dicarboxylate (2. 26g, 9. 8mmol) in DCM (10ml) was added dropwise and stirred for 4h at RT. Evaporated to a residue and purified by chromatography (Companion, 40g silica Redisep column, eluent 15-40% EtOAc/isohexane) to give methyl 2- [4- (2-methyl-quinolin-4- ylmethoxy) -phenyl] propionate (1.25 g, 3.73 mmol) as an orange solid. NMR (CDC13) : 1.45 (d, 3H), 2.70 (s, 3H), 3.60 (s, 3H), 3.65 (m, 1H), 5.45 (s, 2H), 6.95 (d, 2H), 7.20 (d, 2H), 7.40 (s, 1H), 7.45 (t, 1H), 7.65 (t, 1H), 7.85 (d, 1H), 8.00 (d, 1H); MS (M+H) 336.

Reference： [1]Patent: WO2005/85232,2005,A1 .Location in patent: Page/Page column 47
[2]Patent: WO2005/85232,2005,A1 .Location in patent: Page/Page column 52
[3]Patent: WO2005/85232,2005,A1 .Location in patent: Page/Page column 59
[4]Patent: WO2005/85232,2005,A1 .Location in patent: Page/Page column 50
[5]Patent: WO2005/85232,2005,A1 .Location in patent: Page/Page column 55

11
[ 942-54-1 ]
[ 10034-85-2 ]
[ 65784-33-0 ]

Yield	Reaction Conditions	Operation in experiment
6.7g (67%)	With sulfuric acid; acetic acid; In methanol; water;	Methyl 2-(4-hydroxyphenyl)propionate In a mixture of 12ml of hydroiodic acid, 90ml of acetic acid and 1g of phosphorus 10g of 2-(4-methoxyphenyl)propionic acid was refluxed for 3 hours and the reaction mixture was concentrated. 20ml of methanol and 2ml of sulfuric acid were added to the residue and the mixture was refluxed for one hour. After the methanol was concentrated, the water was added to the residue and extracted with ether. The extract was washed over magnesium sulfate and the ether was distilled off. The residue was distilled under reduced pressure to give the object compound having b.p. 150 - 153 C/6mm Hg in a yield of 6.7g (67%)

Reference： [1]Patent: US4016193,1977,A

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[ CAS No. 65784-33-0 ] {[proInfo.proName]}

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[ 65784-33-0 ] Synthesis Path-Upstream 1~1

[ 65784-33-0 ] Synthesis Path-Downstream 1~11

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