N-(4-Chlorophenyl)-3-phenylacrylamide → 5-Chloroquinolin-2(1h)-one
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]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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) trader 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
- temperatureThe reaction mixture was cooled down
- customThe product crystallized out as a pink solid which
- filtrationwas filtered
- customdried
Sources & evidence
- ORD record
- ord-2125b916997c4e6d96420da536d3a807
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05726162
Reaction notes
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