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

HRID 735242Notes

Reaction equation

HRID 735242 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:24])[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[CH3:15].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CCCCCC>CCOC(C)=O>[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])=[CH:18][CH:17]=1)([CH3:15])[C:13](=[O:24])[NH:12]2

Participants

5

Reactant 3

HCID 8058HexaneHCID 2733832Lithium HexamethyldisilazideHCID 688184034,6-Dichloro-2-[2-(4-methoxy-phenyl)-propionylamino]-benzoic acid methyl ester

Product 1

HCID 116746945,7-dichloro-3-(4-methoxy-phenyl)-3-methyl-1H-quinoline-2,4-dioneYield 42%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the example 1, using a 4,6-dichloro-2-[2-(4-methoxy-phenyl)-propionylamino]-benzoic acid methyl ester (1.44 g, 3.77 mmol) and LiHMDS (11.0 mmol, 1M solution in THF). After normal workup, the pure objective compound (0.55 g, 42%) was obtained as yellow solid by a flash column chromatography (n-hexane:EtOAc=10:1): 1H NMR (200 MHz, CDCl3) δ 1.52 (s, 3H, CH3), 3.67 (s, 3H, CO2CH3), 6.89 (d, J=8.9 Hz, 2H, ArH), 6.99-7.08 (m, 3H, ArH), 7.23 (d, J=1.9 Hz, 1H, ArH), 11.25 (s, 1H, NH); m.p. 210-212° C.; MS(EI) m/e 349 [M+], 162, 134; HRMS m/e cacld. for C17H13NO3Cl2 349.0272, found 349.0278.

Workup

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

Sources & evidence

ORD record
ord-e752d633114344c8852f9f24fb347c62
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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