N-(3-Chlorophenyl)-2-methyl-3-phenylacrylamide → 7-Chloro-3-methyl-1H-quinolin-2-one

HRID 1432847Notes

Reaction equation

HRID 1432847 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:19])[C:10]([CH3:18])=[CH:11]C2C=CC=CC=2)[CH:5]=[CH:6][CH:7]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:18]=[C:10]([CH3:11])[C:9](=[O:19])[NH:8]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3497717N-(3-Chlorophenyl)-2-methyl-3-phenylacrylamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 122780437-Chloro-3-methyl-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of N-(3-chlorophenyl)-2-methyl-3-phenylacrylamide (2.5 g, 9.2 mmol) in chlorobenzene (50 mL) is added AlCl3 (6.2 g, 46 mmol). The solution is heated to 120° C. After 4 hours the solution is poured onto ice. The solution is filtered. The organic layer is washed with 1N HCl, H2O and saturated NaCl. The crude product is purified by column chromatography eluting with 2% MeOH/CH2Cl2. The title compound is obtained as a white solid (1.5 g, 7.74 mmol). 1H NMR (d6-DMSO, 300 MHz) δ11.82 (bs, 1H), 7.73 (s, 1H), 7.52 (m, 1H), 7.21 (m, 2H), 2.08 (s, 3H).

Workup

  1. additionAfter 4 hours the solution is poured onto ice
  2. filtrationThe solution is filtered
  3. washThe organic layer is washed with 1N HCl, H2O and saturated NaCl
  4. customThe crude product is purified by column chromatography
  5. washeluting with 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-644852ca47b5481583d39c05a0cc5fff
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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