Aniline → 3-(4-Methoxy-3-methyl-benzoyl)-1H-quinolin-4-one

HRID 227004Notes

Reaction equation

HRID 227004 reaction equation
CO[C:3](=[O:20])[C:4]([C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([CH3:18])[CH:11]=1)=[CH:5]OCC.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]([C:4]2[C:3](=[O:20])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:5]=2)=[O:19])=[CH:11][C:12]=1[CH3:18]

Participants

4

Reactant 2

HCID 6115AnilineHCID 668786263-Ethoxy-2-(4-methoxy-3-methyl-benzoyl)-acrylic acid methyl ester

Product 1

HCID 577547583-(4-Methoxy-3-methyl-benzoyl)-1H-quinolin-4-oneYield 101%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Experimental conditions analogous to those described for Step 1 of Example 1 were used with 1 g (3.78 mmol) of 3-ethoxy-2-(4-methoxy-3-methyl-benzoyl)-acrylic acid methyl ester, 0.214 g (3.78 mmol) of aniline, and 20 mL of diphenyl ether to yield 1.12 g of 3-(4-Methoxy-3-methyl-benzoyl)-1H-quinolin-4-one.

Sources & evidence

ORD record
ord-cd23c874ceec475c8f9c1e82dc654fdd
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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