Dichloromethane → 5,7-dichloro-3-(4-methoxy-3-nitro-phenyl)-3-methyl-1H-quinoline-2,4-dione

HRID 735249Notes

Reaction equation

HRID 735249 reaction equation
C[O:2][C:3](=O)[C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:27])[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([N+:24]([O-:26])=[O:25])[CH:17]=1)[CH3:15].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.ClCCl>CO>[Cl:10][C:9]1[CH:8]=[C:7]([Cl:11])[CH:6]=[C:5]2[C:4]=1[C:3](=[O:2])[C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([N+:24]([O-:26])=[O:25])[CH:17]=1)([CH3:15])[C:13](=[O:27])[NH:12]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2733832Lithium HexamethyldisilazideHCID 688191894,6-Dichloro-2-[2-(4-methoxy-3-nitro-phenyl)-propionylamino]-benzoic acid methyl ester

Product 1

HCID 116540895,7-dichloro-3-(4-methoxy-3-nitro-phenyl)-3-methyl-1H-quinoline-2,4-dioneYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The objective compound was prepared by the same procedure for the example 13, using a 4,6-dichloro-2-[2-(4-methoxy-3-nitro-phenyl)-propionylamino]-benzoic acid methyl ester (0.20 g, 0.47 mmol) and LiHMDS (1.40 mmol, 1M THF solution). After normal workup, the objective compound (120 mg, 71%) was obtained as yellow solid by a flash column chromatography (dichloromethane:methanol=30:1): 1H NMR (200 MHz, DMSO-d6) δ 1.60 (s, 3H, CH3), 3.86 (s, 3H, OCH3), 7.05 (d, J=2.0 Hz, 1H, ArH), 7.29-7.37 (m, 2H, ArH), 7.61 (d, J=2.0 Hz, 1H, ArH); m.p. 255-256° C.; MS(EI) m/e 394 [M+], 207, 132, 119; HRMS m/e cacld. for C17H12N2O5Cl2 394.0123, found 394.0114.

Workup

  1. customThe objective compound was prepared by the same procedure for the example 13

Sources & evidence

ORD record
ord-d7868e7f190140bb98a76bf00be97255
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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