Lithium Hexamethyldisilazide → 6,7-dichloro-3-methyl-3-phenyl-1H-quinoline-2,4-dione

HRID 735240Notes

Reaction equation

HRID 735240 reaction equation
CO[C:3](=[O:23])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:22])[CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>CCOC(C)=O>[Cl:10][C:8]1[CH:9]=[C:4]2[C:5](=[CH:6][C:7]=1[Cl:11])[NH:12][C:13](=[O:22])[C:14]([CH3:15])([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:3]2=[O:23]

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 688158724,5-Dichloro-2-(2-phenyl-propionylamino)-benzoic acid methyl ester

Product 1

HCID 116167296,7-dichloro-3-methyl-3-phenyl-1H-quinoline-2,4-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the example 1, using a 4,5-dichloro-2-(2-phenyl-propionyl amino)-benzoic acid methyl ester (1.00 g, 2.84 mmol) and LiHMDS (8.52 mmol, 1M solution in THF). After normal workup, the pure objective compound (0.36 g, 40%; yellow solid) was obtained by a flash column chromatography (Hex:EtOAc=4:1): 1H NMR (200 MHz, CDCl3) δ 1.83 (s, 3H, CH3), 7.02 (s, 1H, ArH), 7.23-7.33 (m, 5H, ArH), 7.97 (s, 1H, ArH), 8.41 (br s, 1H, NH); m.p. 213-214° C.; MS(EI) m/e 319 [M+], 285, 132, 104 ; HRMS m/e cacld. for C16H11NO2Cl 319.0167, found 319.0168.

Workup

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

Sources & evidence

ORD record
ord-097309c66c8c4307a92837bb6d0ec1e7
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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