Aluminum(III) Chloride → 7,8-Difluoroquinolin-2(1H)-one

HRID 255176Notes

Reaction equation

HRID 255176 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:19])/[CH:11]=[CH:12]/C1C=CC=CC=1.[Cl-].[Cl-].[Cl-].[Al+3].BrC1C=C2C(C=CC(=O)N2)=CC=1>>[F:8][C:7]1[C:2]([F:1])=[C:3]2[C:4]([CH:12]=[CH:11][C:10](=[O:19])[NH:9]2)=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 142210257-Bromoquinolin-2(1H)-oneHCID 47450756(2E)-N-(2,3-difluorophenyl)-3-phenylacrylamide2×

Product 1

HCID 642086717,8-Difluoroquinolin-2(1H)-one

Procedure

The compound was prepared from (2E)-N-(2,3-difluorophenyl)-3-phenylacrylamide (Intermediate 22) (7.4 g, 28.5 mmol) and aluminium trichloride (19 g, 142 mmol) as described for Intermediate 17. The crude cyclization product was obtained as a single regioisomer, which was used without further purification, 2 g light brown solid (37%).

Workup

  1. customThe crude cyclization product was obtained as a single regioisomer, which
  2. customwas used without further purification, 2 g light brown solid (37%)

Sources & evidence

ORD record
ord-3092021686104b8a9f1c2d003bb94370
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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