Ammonia → 2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)-2-(4-chlorophenyl)acetamide
Reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH:13]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[C:14]([O:16]C)=O)[C:7]2=[O:12].[NH3:25]>CO>[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH:13]([C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)[C:14]([NH2:25])=[O:16])[C:7]2=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A pressure tube was charged with methyl 2-(5-amino-1-oxoisoquinolin-2(1H)-yl)-2-(4-chlorophenyl)acetate (1.35 g, 0.00394 mol) and ammonia in methanol (7 mL, 2M solution) was added and the reaction heated at 70° C. for 16 hours. The reaction mixture was cooled to room temperature and checked for completion. The reaction was only 20% complete. Further heating of the reaction for another 6 hours did not seem to help in the progress of the reaction. The solvent was removed and the residue was purified by flash chromatography to obtain the product as a light yellow solid. MS m/z=328.2 (M+H).
Workup
- additionwas added
- temperatureThe reaction mixture was cooled to room temperature
- temperatureFurther heating of the reaction for another 6 hours
- customto help in the progress of the reaction
- customThe solvent was removed
- customthe residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-f3496e1b794743e1b2cab0308d1cfeec
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816371B2
Reaction notes
Loading…