N-(3-methoxyphenyl)-3-phenylprop-2-enamide → 7-Hydroxycarbostyril

HRID 1750079Notes

Reaction equation

HRID 1750079 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C[O:6][C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:23])[CH:15]=[CH:16]C2C=CC=CC=2)[CH:10]=[CH:11][CH:12]=1>ClC1C=CC=CC=1>[OH:6][C:7]1[CH:8]=[C:9]2[C:10]([CH:16]=[CH:15][C:14](=[O:23])[NH:13]2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 583041N-(3-methoxyphenyl)-3-phenylprop-2-enamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 109757877-HydroxycarbostyrilYield 53%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

AlCl3 (11.5 g, 86.3 mmol) was added portion-wise to a suspension of intermediate 13 (4.2 g, 16.6 mmol) in chlorobenzene (90 mL) at 0° C. The reaction mixture was gradually warmed to 120° C. and stirred for 3 h. The mixture was poured into ice water and the resulting precipitate was collected by filtration, washed with water, and purified by flash chromatography on silica gel column (elution with DCM/MeOH=60:1) to give 7-hydroxyquinolin-2(1H)-one (intermediate 14) (1.41 g, 53%) as a white solid.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with water
  3. custompurified by flash chromatography on silica gel column (elution with DCM/MeOH=60:1)

Sources & evidence

ORD record
ord-06571f80273c41a2ac5c54623e659354
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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