Ammonia → 4,5-dichloro-2,3-dihydro-1H-isoindol-1-one
Reaction equation
[NH3:1].Br[CH2:3][C:4]1[C:14]([Cl:15])=[C:13]([Cl:16])[CH:12]=[CH:11][C:5]=1[C:6](OCC)=[O:7]>CN(C)C=O>[Cl:15][C:14]1[C:13]([Cl:16])=[CH:12][CH:11]=[C:5]2[C:4]=1[CH2:3][NH:1][C:6]2=[O:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Ammonia was bubbled through a solution of ethyl 2-bromomethyl-3,4-dichlorobenzoate (25 g, 0.08 mol.) in 250 ml. of dimethylformamide for 1/2 hour at 0° C. The mixture was stirred for one hour at 25° C., poured on crushed ice and filtered. The solid was chromatographed on silica gel eluted ether, ethyl acetate and then acetone to give 4,5-di-chloro-2,3-dihydro-1H-isoindol-1-one.
Workup
- additionpoured
- customon crushed ice
- filtrationfiltered
- customThe solid was chromatographed on silica gel
- washeluted ether, ethyl acetate
Sources & evidence
- ORD record
- ord-caca1a2d4551429e9db89dfde2c52b62
- Source dataset
- uspto-grants-1980_08
- Patent number
- US04218464
Reaction notes
Loading…