19008-43-6|Benzyl 4-aminobenzoate| Ambeed

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Quality Control of [ 19008-43-6 ] Purity: 98% SDS Specification

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Product Details of [ 19008-43-6 ]

CAS No. :	19008-43-6
Formula :	C₁₄H₁₃NO₂
M.W :	227.26
SMILES Code :	O=C(OCC1=CC=CC=C1)C2=CC=C(N)C=C2
MDL No. :	MFCD00626894
InChI Key :	DAOPOOMCXJPWPK-UHFFFAOYSA-N
Pubchem ID :	98488

Safety of [ 19008-43-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 19008-43-6 ]

* 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 [ 19008-43-6 ]

[ 19008-43-6 ] Synthesis Path-Downstream 1~35

1
[ 14786-27-7 ]
[ 19008-43-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With tin(II) chloride dihdyrate; In tetrahydrofuran; at 45℃; for 3h;	Step 2: Synthesis of benzyl 4-aminobenzoate (187) Benzyl 4-nitrobenzoate (1.5 g, 5.83 mmol) was dissolved in THF (40 ml), SnCl2 dihydrate (5.92 g, 26.2 mmol) was added and the mixture was stirred at 45 C. for 3 hours. NaHCO3 s.s. and EtOAc were added to the reaction mixture that was filtered on a celite pad. The solution was separated and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over sodium sulfate and the solvent was evaporated. The desired product was obtained as a pale yellow solid (1.25 g, 5.50 mmol, 94% yield, MS/ESI+ 228.1 [MH]+) and used in the following step without further purification.
	With hydrogen;nickel; In 1,4-dioxane; under 3750.38 Torr; for 16h;	10.01 g 4-nitrobenzoic acid is suspended in 500 mL acetonitrile and then combined with 15.03 g (108.7 mmol, 1.2 eq) potassium carbonate. 15.40 g (171.0 mmol, 1 eq) benzylbromide ais added dropwise with stirring and the reaction mixture is then heated to 60 C. for 5 h with stirring. It is combined with 750 ml distilled water, extracted 4× with 250 mL EE and, after the organic phases have been combined, dried on sodium sulphate. After the elimination of all the volatile constituents in vacuo the crude product is successively suspended 2× in toluene and all the volatile constituents are eliminated in vacuo (removal of excess benzylbromide). 20.60 g (80.1 mmol) benzyl 4-nitro-benzoate is obtained as a colourless solid, which is used in the next step without further purification. 20.6 g of the benzyl 4-nitro-benzoate are dissolved in 350 mL dioxane and this solution is combined with 6.9 g (49.9 mmol, 0.61 eq) Raney nickel. The mixture is hydrogenated for 16 h with stirring at 5 bar H2 pressure. The catalyst is filtered off, all the volatile constituents are eliminated in vacuo. 17.0 g (74.8 mmol, 93%) benzyl 4-aminobenzoate is obtained in the form of a colourless solid.
	With hydrogen;nickel; In 1,4-dioxane; under 3750.38 Torr; for 16h;	20.6 g of the benzyl 4-nitrobenzoate are dissolved in 350 mL dioxane and this solution is combined with 6.9 g (49.9 mmol, 0.61 eq) Raney nickel. The mixture is hydrogenated for 16 h with stirring at 5 bar of H2 pressure. The catalyst is filtered off, all the volatile constituents are eliminated in vacuo and 17 g of D-I are obtained.

	With hydrogen;nickel; In 1,4-dioxane; under 3750.38 Torr; for 16h;	20.6 g of the benzyl 4-nitrobenzoate are dissolved in 350 mL dioxane and this solution is combined with 6.9 g (49.9 mmol, 0.61 eq) Raney nickel. The mixture is hydrogenated at 5 bar H2 pressure for 16 h with stirring. The catalyst is filtered off and all the volatile constituents are eliminated in vacuo. 17g benzyl 4-aminobenzoate are obtained.
2.93 g	With ammonium chloride; zinc; In water; acetone; at 0 - 20℃; for 1h;	Compound 4. To a solution of benzyl 4-nitrobenzoate (3, 3.76 g, 14.62 mmol) in acetone (40 mL) at 0 C was added zinc dust (4.78 g, 73.1 mmol) followed by a solution of ammonium chloride (7.82 g, 146 mmol) in water. After stirring at RT for lh, the reaction wasfiltered through CELITETM filter medium and then concentrated in vacuo. The residue was suspended in ethyl acetate, washed with water followed by brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography using an Isco 80 g column eluting with 0-50% ethyl acetate/hexanes to give benzyl 4- aminobenzoate 4 (2.93 g, 12.89 mmol, 88 ield) as a white solid. ‘HNIVIR (CDC13) 7.91(d,2H), 7.30-7.41(m, 5H), 6.65(d, 2H), 5.33(s, 2H), 4.12(s, 2H); MS(ESI) m/z 228 (M+H)t

References: [1]Advanced Synthesis and Catalysis,2008,vol. 350,p. 406 - 410.
[2]ChemCatChem,2018,vol. 10,p. 505 - 509.
[3]Patent: US2014/155391,2014,A1 .Location in patent: Paragraph 0549; 0551.
[4]Journal of the American Chemical Society,2015,vol. 137,p. 7608 - 7611.
[5]Tetrahedron Letters,2000,vol. 41,p. 175 - 177.
[6]Journal of Medicinal Chemistry,2014,vol. 57,p. 3856 - 3873.
[7]Organic Letters,2005,vol. 7,p. 5023 - 5026.
[8]Journal of the American Chemical Society,1921,vol. 43,p. 364.
[9]Journal of the Indian Chemical Society,1930,vol. 7,p. 577,583.
[10]Journal of the American Chemical Society,1921,vol. 43,p. 364.
[11]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 1749 - 1761.
[12]Patent: US2007/32514,2007,A1 .Location in patent: Page/Page column 14-15.
[13]Patent: WO2008/77885,2008,A2 .Location in patent: Page/Page column 29.
[14]Patent: US2009/163467,2009,A1 .Location in patent: Page/Page column 8.
[15]Patent: WO2016/144608,2016,A1 .Location in patent: Paragraph 0017; 0055.

2
[ 19008-43-6 ]
[ 150374-99-5 ]
4-[4-(2,2-Dimethyl-propionyloxy)-benzenesulfonylamino]-benzoic acid benzyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,1996,vol. 4,p. 2115 - 2134.

3
[ 19008-43-6 ]
[ 193156-93-3 ]
[ 261724-38-3 ]

References: [1]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 2823 - 2833.

4
[ 19008-43-6 ]
C₂₃H₂₉N₃O₆ [ No CAS ]
[ 325464-52-6 ]

References: [1]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 1964 - 1972.

5
[ 19008-43-6 ]
C₂₃H₂₉N₃O₇ [ No CAS ]
[ 325464-50-4 ]

References: [1]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 1964 - 1972.

6
[ 191934-25-5 ]
[ 19008-43-6 ]

Yield	Reaction Conditions	Operation in experiment
90%		To a solution of ester 8a (1.91 g, 5.82 mmol) in dry DCM (36 mL) was added TFA (12 mL) and the mixture stirred at room temperature for 1 h. The solution was quenched with ice (25 mL) and neutralised (NaHCO3). The organic layer was collected and the aqueous layer extracted with DCM (3×50 mL). The organic extracts were combined and washed with saturated aqueous sodium bicarbonate solution (120 mL), water (2×120 mL) and dried (Na2SO4). The solvent was removed in vacuo to give the title product 75a (1.19 g, 90%) as a golden brown solid, which was used without further purification. Mp 94-95 C [lit.17 Mp 90 C]; Rf=0.25 (CH2Cl2/MeOH=9:1); 1H NMR (400 MHz, CDCl3) 3.90 (2H, br s, NH2), 5.31 (2H, s, ArCH2), 6.63 (2H, d, J=8.4 Hz, Ar-H), 7.25-7.39 (5H, m, Ar-H), 7.59 (2H, d, J=8.4 Hz, Ar-H). Spectroscopic data were in agreement with literature values.18

References: [1]Tetrahedron,2012,vol. 68,p. 1790 - 1801.
[2]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 1964 - 1972.

7
[ 19008-43-6 ]
[ 97506-01-9 ]
[ 869627-61-2 ]