Ethyl Acetate → 4,6-Dichloro-2-(2-(4-nitro-phenyl)-propionylamino]-benzoic acid methyl ester

HRID 735228Notes

Reaction equation

HRID 735228 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:14])[C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].O=S(Cl)Cl.[CH3:19][O:20][C:21](=[O:31])[C:22]1[C:27]([Cl:28])=[CH:26][C:25]([Cl:29])=[CH:24][C:23]=1[NH2:30].C(OCC)(=O)C>C(OCC)C>[CH3:19][O:20][C:21](=[O:31])[C:22]1[C:27]([Cl:28])=[CH:26][C:25]([Cl:29])=[CH:24][C:23]=1[NH:30][C:11](=[O:13])[CH:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[CH3:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 892442-(4-Nitrophenyl)propionic acidHCID 12363232Methyl 2-amino-4,6-dichlorobenzoate

Product 1

HCID 688202774,6-Dichloro-2-(2-(4-nitro-phenyl)-propionylamino]-benzoic acid methyl esterYield 99.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The objective compound was prepared by the same procedure for the intermediate 1, using a 2-(4-nitro-phenyl)-propionic acid (1.40 g, 7.17 mmol), SOCl2 (5.1 mL, 71.7 mmol), and 2-amino-4,6-dichloro-benzoic acid methyl ester (1.6 g, 5.74 mmol). After normal workup, the pure objective compound (2.26 g, 99%) was obtained as pale yellow solid by recrystallization (ethyl acetate:ethyl ether=1:5): 1H NMR (200 MHz, CDCl3) δ 1.63 (d, J=7.1 Hz, 3H, CH3), 3.85-3.86 (m, 4H, CO2CH3 & CH), 7.18 (d, J=2.0 Hz, 1H, ArH), 7.54 (d, J=8.7 Hz, 2H, ArH), 8.24 (d, J=8.7 Hz, 2H, ArH), 8.45 (d, J=2.0 Hz, 1H, ArH), 9.59 (br s, 1H, ArH).

Sources & evidence

ORD record
ord-89736d81ff8c49d38e71b2803c0cc0ad
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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