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

HRID 1497202Notes

Reaction equation

HRID 1497202 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[C:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]([F:27])([F:26])[F:25])=[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:16]=1[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]([F:25])([F:26])[F:27])=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)=[O:28])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86683024N-[4-Chloro-2-(2-trifluoromethyl-phenylethynyl)-phenyl]-malonamic acid ethyl ester

Product 1

HCID 866830256-Chloro-2-oxo-4-(2-trifluoromethyl-benzyl)-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-trifluoromethyl-phenylethynyl)-phenyl]-malonamic acid ethyl ester (213 mg, 0.52 mmol) and NaH (31.2 mg, 0.78 mmol) in DMSO. Off white solid (95 mg, 45%). MS (ESI): 410 (M+H)+.

Sources & evidence

ORD record
ord-7321ed9b73fe4b10ba9019721b4d7968
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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