Dichloromethane → 4,6-Dichloro-2-[2-(4-methoxy-3-nitro-phenyl)-propionylamino]-benzoic acid methyl ester

HRID 735232Notes

Reaction equation

HRID 735232 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([OH:12])=O)=[CH:5][C:4]=1[N+:14]([O-:16])=[O:15].[CH3:17][O:18][C:19](=[O:29])[C:20]1[C:25]([Cl:26])=[CH:24][C:23]([Cl:27])=[CH:22][C:21]=1[NH2:28].ClCCl>CCCCCC>[CH3:17][O:18][C:19](=[O:29])[C:20]1[C:25]([Cl:26])=[CH:24][C:23]([Cl:27])=[CH:22][C:21]=1[NH:28][C:10](=[O:12])[CH:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([N+:14]([O-:16])=[O:15])[CH:5]=1)[CH3:13]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 12363232Methyl 2-amino-4,6-dichlorobenzoateHCID 214441642-(4-Methoxy-3-nitrophenyl)propanoic acid

Product 1

HCID 688191894,6-Dichloro-2-[2-(4-methoxy-3-nitro-phenyl)-propionylamino]-benzoic acid methyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The objective compound was prepared by the same procedure for the intermediate 1, using a 2-(4-methoxy-3-nitro-phenyl)-propionic acid (0.60 g, 2.70 mmol), SOC2 (0.96 mL, 13.0 mmol), and 2-amino-4,6-dichloro-benzoic acid methyl ester (0.77 g, 3.50 mmol). After normal workup, the pure objective compound (0.98 g, 82%) was obtained as white solid by recrystallization (dichloromethane:n-hexane=1:3): m.p 122° C.; 1H NMR (200 MHz, CDCl3) δ 1.60 (d, J=7.2 Hz, 3H, CH3), 3.65-3.84 (m, 4H, CO2CH3 & CH), 7.55 (dd, J=8.8, 2.2 Hz, 1H, ArH), 7.84 (d, J=2.2 Hz, 1H, ArH), 8.44 (d, J=2.0 Hz, 1H, ArH), 9.51 (br s, 1H, NH).

Sources & evidence

ORD record
ord-0b2c88134286432a9ab251a4f2e519bd
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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