1-(3-Chloro-benzyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide → 1-(3-Chloro-benzyl)-3-(4-methoxy-benzoyl)-1H-quinolin-4-one

HRID 227084Notes

Reaction equation

HRID 227084 reaction equation
CON(C)[C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[CH:7]=1)=[O:5].[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([Mg]Br)=[CH:30][CH:29]=1>C1COCC1>[Cl:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:15](=[O:16])[C:6]([C:4](=[O:5])[C:31]2[CH:32]=[CH:33][C:28]([O:27][CH3:26])=[CH:29][CH:30]=2)=[CH:7]1

Participants

4

Reactant 2

HCID 577546151-(3-Chloro-benzyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amideHCID 178491912HCID 178491912, compound

Product 1

HCID 577547841-(3-Chloro-benzyl)-3-(4-methoxy-benzoyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60, from 300 mg (0.84 mmol) of 1-(3-chloro-benzyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 3 mL THF and 3.7 mL 0.5M 4-methoxyphenylmagnesium bromide. Yield: 168 mg of a white solid. LC-MSD, m/z for C24H18ClNO3 [M+H]+=404.1, 406.0; HPLC retention time: 2.4 min.

Sources & evidence

ORD record
ord-91a7c42bb7824b99a5c4610f754a7375
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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