Sodium hydride → 6-Chloro-4-(2-chloro-benzyl)-2-oxo-8-trifluoromethyl-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester

HRID 1497190Notes

Reaction equation

HRID 1497190 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C:6]([NH:8][C:9]1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][C:12]([Cl:19])=[CH:11][C:10]=1[C:20]#[C:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:28])=[O:7])[CH3:2].[H-].[Na+]>CS(C)=O>[CH2:1]([O:3][C:4]([C:5]1[C:6](=[O:7])[NH:8][C:9]2[C:10]([C:20]=1[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:28])=[CH:11][C:12]([Cl:19])=[CH:13][C:14]=2[C:15]([F:17])([F:18])[F:16])=[O:29])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86683016N-[4-Chloro-2-(2-chloro-phenylethynyl)-6-trifluoromethyl-phenyl]-malonamic acid ethyl ester

Product 1

HCID 866830176-Chloro-4-(2-chloro-benzyl)-2-oxo-8-trifluoromethyl-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in analogy to example 29 step B from N-[4-chloro-2-(2-chloro-phenylethynyl)-6-trifluoromethyl-phenyl]-malonamic acid ethyl ester (1 g, 2.25 mmol) and NaH (140 mg, 3.38 mmol) in DMSO (10 ml). Off white solid (450 mg, 45%). LC-MS (ESI): 444 (M+H)+.

Sources & evidence

ORD record
ord-15d7be18941b4ee487e924e39830d96b
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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