Aluminum(III) Chloride → 5,7-Difluoro-1,2-dihydroquinolin-2-one

HRID 255179Notes

Reaction equation

HRID 255179 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:19])/[CH:11]=[CH:12]/C2C=CC=CC=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[Cl-].[Cl-].[Cl-].[Al+3].FC1C(F)=C2C(C=CC(=O)N2)=CC=1>>[F:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[C:4]2[C:5]=1[CH:12]=[CH:11][C:10](=[O:19])[NH:9]2

Participants

4

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 17271861HCID 17271861, compound2×HCID 642086717,8-Difluoroquinolin-2(1H)-one

Product 1

HCID 642082495,7-Difluoro-1,2-dihydroquinolin-2-one

Procedure

The compound was prepared from (2E)-N-(3,5-difluorophenyl)-3-phenylacrylamide (Intermediate 26) (8.1 g, 31.2 mmol) and aluminium trichloride (21 g, 156 mmol) in a similar way as described for Intermediate 21. 3.47 g light brown solid (61%), mp 292-318° C.

Sources & evidence

ORD record
ord-d0a2ca0a36e34e86af971ccd477f06f9
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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