Hexane → 3-(4-bromo-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione

HRID 735246Notes

Reaction equation

HRID 735246 reaction equation
CO[C:3](=[O:24])[C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:23])[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1)[CH3:15].[H-].[Na+].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CCCCCC>CCOC(C)=O>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]2([CH3:15])[C:3](=[O:24])[C:4]3[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][C:9]=3[Cl:10])[NH:12][C:13]2=[O:23])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 2733832Lithium HexamethyldisilazideHCID 688165642-[2-(4-Bromo-phenyl)-propionylamino]-4,6-dichlorobenzoic acid methyl ester

Product 1

HCID 115603623-(4-bromo-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dioneYield 18%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the example 1, using a 2-[2-(4-bromo-phenyl)-propionyl amino]-4,6-dichloro-benzoic acid methyl ester (400 mg, 0.93 mmol) and NaH (78 mg, 1.95 mmol) as a base instead of LiHMDS. After normal workup, the objective compound (60 mg, 18%) was obtained as white solid by a flash column chromatography (n-hexane:EtOAc=5:1): 1H NMR (200 MHz, CDCl3+CD3OD) δ 1.69 (s, 3H, CH3), 6.91-7.48 (m , 6H, ArH); m.p. 237-238° C.; MS(EI) m/e 397 [M+].

Workup

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

Sources & evidence

ORD record
ord-8ee734c2109340dda1f22ffd2c677d28
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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