Trifluoroacetic acid → Isoindoline-5-carbonitrile
Reaction equation
C(OC([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]#[N:18])[CH:14]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:17]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:16]2)#[N:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
A mixture of 2-(tert-butyloxycarbonyl)-5-cyano-2,3-dihydro-1H-isoindole (7.6 g) and trifluoroacetic acid (20 ml) in dichloromethane (200 ml) was heated at 40° C. for 0.5 h, then cooled and evaporated in vacuo and the residue partitioned between dichloromethane and 2M sodium hydroxide. The aqueous phase was re-extracted with dichloromethane and the combined organics dried and evaporated to give the title compound as a pink solid (4.24 g, 94%).