4-Methoxyphenylacetic Acid → 7-chloro-3-(4-methoxyphenyl)-1H-quinolin-2-one

Reaction equation

[NH2:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4]O.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20](O)=[O:21])=[CH:15][CH:14]=1>>[Cl:10][C:8]1[CH:9]=[C:2]2[C:3]([CH:4]=[C:19]([C:16]3[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=3)[C:20](=[O:21])[NH:1]2)=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 76904-Methoxyphenylacetic Acid

HCID 4134900(2-Amino-4-chlorophenyl)methanol

Product 1

HCID 122780417-chloro-3-(4-methoxyphenyl)-1H-quinolin-2-one

Procedure

2-Amino-4-chlorobenzyl alcohol (4 g, 25.3 mol) and 4-methoxyphenyl acetic acid (14.0 g, 76.4 mmol) were reacted in a similar manner to that described in Example 19 to give 7-chloro-3-(4-methoxyphenyl)-2(1H)-quinolone; mp 256°-257° C. (ethyl acetate).

Sources & evidence

ORD record: ord-f5dd0505cc9546ce813bbffe2d636fcd
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05614532

Reaction notes

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