(2E)-N-(3-fluorophenyl)-3-phenyl-2-propenamide → 7-Fluoroquinolin-2(1H)-one

HRID 255182Notes

Reaction equation

HRID 255182 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:18])/[CH:10]=[CH:11]/C2C=CC=CC=2)[CH:5]=[CH:6][CH:7]=1.[Cl-].[Cl-].[Cl-].[Al+3].FC1C(F)=C2C(C=CC(=O)N2)=CC=1>>[F:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:11]=[CH:10][C:9](=[O:18])[NH:8]2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 727184(2E)-N-(3-fluorophenyl)-3-phenyl-2-propenamide2×HCID 6451240Aluminum(III) ChlorideHCID 642086717,8-Difluoroquinolin-2(1H)-one

Product 1

HCID 190675757-Fluoroquinolin-2(1H)-one

Procedure

The compound was prepared from (2E)-N-(3-fluorophenyl)-3-phenylacrylamide (Intermediate 30) (13.8 g, 57.2 mmol) and aluminium trichloride (30.5 g, 229 mmol) in a similar way as described for Intermediate 21 to give a mixture of the title compound together with the corresponding 5-fluoro regioisomer in a ratio of 3:1. This mixture was vigorously stirred in dichloromethane (100 mL) for 3 hours at room temperature and then filtered. The solid obtained was resuspended in diethyl ether (200 mL) and stirred like above and filtered to give 3.63 g (34%) of the crude product containing 12% of the 5-fluoro regioisomer. This was used without further purification for the next step.

Workup

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Sources & evidence

ORD record
ord-fa9f7cb75ff2413a874fb583c27a9be0
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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