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

HRID 735250Notes

Reaction equation

HRID 735250 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:26])[C:5]([C:15]1[CH:20]=[CH:19][C:18]([O:21]C)=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=1)([CH3:14])[C:6](=[O:13])[NH:7]2.B(Br)(Br)Br.ClCCl>CO>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:26])[C:5]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=1)([CH3:14])[C:6](=[O:13])[NH:7]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 116540895,7-dichloro-3-(4-methoxy-3-nitro-phenyl)-3-methyl-1H-quinoline-2,4-dione

Product 1

HCID 116537995,7-dichloro-3-(4-hydroxy-3-nitro-phenyl)-3-methyl-1H-quinoline-2,4-dioneYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The objective compound was prepared by the same procedure for the example 13, using a 5,7-dichloro-3-(4-methoxy-3-nitro-phenyl)-3-methyl-1H-quinoline-2,4-dione (0.12 g, 0.30 mmol) and BBr3 (0.90 mL, 1.0 M dichloromethane solution). After normal workup, the objective compound (50 mg, 48%) was obtained as pale yellow solid by a flash column chromatography (dichloromethane:methanol=30:1): 1H NMR (200 MHz, DMSO-d6) δ 1.58 (s, 3H, CH3), 7.05-7.09 (m, 2H, ArH), 7.14-7.31 (m, 2H, ArH), 7.61 (d, J=2.4 Hz, 1H, ArH); m.p. 239-240° C.; MS(EI) m/e 380 [M+], 193, 165, 135; HRMS m/e cacld. for C16H10N2O5Cl2 379.9967, found 379.9968.

Workup

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

Sources & evidence

ORD record
ord-de5f2b92f76d4cc4be5b809667b8e46b
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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