N-(4-Chlorophenyl)-3-phenylacrylamide → 5-Chloroquinolin-2(1h)-one

HRID 2122

Reaction equation

HRID 2122 reaction equation
ClC1C=CC([NH:8][C:9](=[O:18])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=CC=1.[Cl-:19].[Al+3].[Cl-].[Cl-]>ClC1C=CC=CC=1>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[CH:11]=[CH:10][C:9](=[O:18])[NH:8]2

Participants

4

Reactant 2

HCID 303259N-(4-Chlorophenyl)-3-phenylacrylamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 122780365-Chloroquinolin-2(1h)-one

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
125 °C

Procedure

To a mixture of N-(4-chlorophenyl)cinnamamide (8.3 g), and chlorobenzene (60 ml) was added portionwise aluminum chloride (21.4 g) under nitrogen at room temperature and the reaction mixture was slowly warmed up to 125° C. and kept at that temperature for 3 hours. The reaction mixture was cooled down and poured over 400 g of ice. The product crystallized out as a pink solid which was filtered and dried.

Workup

  1. temperatureThe reaction mixture was cooled down
  2. customThe product crystallized out as a pink solid which
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-771487d5281b4f96990cdc8a7a9c2bb2
Source dataset
uspto-grants-1998_03
Patent number
US05728698

Linked notes

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