N-(3-fluorophenyl)-3-phenylacrylamide → 7-Fluoroquinolin-2(1H)-one

HRID 1644303Notes

Reaction equation

HRID 1644303 reaction equation
F[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.FC1C=C(NC(=O)C=CC2C=CC=CC=2)C=CC=1.[Cl-].[Cl-].[Cl-].[Al+3].FC1C(F)=C2C(C=CC(=O)N2)=CC=1>>[F:8][C:6]1[CH:5]=[C:4]2[C:3]([CH:12]=[CH:11][C:10](=[O:19])[NH:9]2)=[CH:2][CH:7]=1

Participants

5

Reactant 4

HCID 727183N-(3-fluorophenyl)-3-phenylacrylamide2×HCID 6451240Aluminum(III) ChlorideHCID 17271861HCID 17271861, compoundHCID 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-99049a5c6890403c8de07598a61320ea
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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