Pyridine → Methyl 4-amino-3-(4-methoxybenzamido)benzoate

HRID 252820Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[NH2:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[NH2:23])[C:16]([O:18][CH3:19])=[O:17].N1C=CC=CC=1>CC#N>[NH2:23][C:22]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=1[NH:12][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-methoxybenzoyl chloride (1.03 g, 6.02 mmol) in CH3CN (6 ml) was added drop wise to a solution of methyl 3,4-diaminobenzoate (106) (1.00 g, 6.02 mmol) and pyridine (0.49 ml, 6.02 mmol) in CH3CN (25 ml) at 0° C. The reaction mixture was stirred for 3 h at 0° C. and the solvent was evaporated. Ethyl acetate was added and the organic layer was washed successively with saturated solutions of NH4Cl, NaHCO3 and NaCl, dried over MgSO4, filtered and concentrated. After purification by flash chromatography on silica gel (eluent 1-3% MeOH in DCM), 1.03 g (56%) of compound 107 was obtained as a off white solid. 1H NMR: (DMSO) δ(ppm): 9.51 (s, 1H), 7.96 (d, J=8.8 Hz, 2H), 7.75 (d, J=2.0 Hz, 1H), 7.56 (dd, J=8.4, 2.0 Hz, 1H), 7.03 (d, J=9.0 Hz, 2H), 6.75 (d, J=8.4 Hz, 1H), 5.80 (s, 2H), 3.83 (s, 3H), 3.75 (s, 3H). MS: (calc.) 300.1; (obt.) 301.1 (MH)+.

Workup

customthe solvent was evaporated
additionEthyl acetate was added
washthe organic layer was washed successively with saturated solutions of NH4Cl, NaHCO3 and NaCl
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customAfter purification by flash chromatography on silica gel (eluent 1-3% MeOH in DCM)

Sources & evidence

ORD record: ord-0b7f14e14d854d7f8ff85d294e6e82a3
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868205B2

Reaction notes

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