Trifluoroacetic acid → 2,3-Dihydro-1H-isoindole-5-carbonitrile

HRID 1059722Notes

Reaction equation

HRID 1059722 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

HCID 6422Trifluoroacetic acidHCID 18630967tert-Butyl 5-cyano-1,3-dihydro-2H-isoindole-2-carboxylate

Product 1

HCID 179862802,3-Dihydro-1H-isoindole-5-carbonitrileYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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%).

Workup

  1. temperaturecooled
  2. customevaporated in vacuo
  3. customthe residue partitioned between dichloromethane and 2M sodium hydroxide
  4. extractionThe aqueous phase was re-extracted with dichloromethane
  5. customthe combined organics dried
  6. customevaporated

Sources & evidence

ORD record
ord-b72684da16574146b15d0f3a6239c5e5
Source dataset
uspto-grants-2003_02
Patent number
US06521638B1

Reaction notes

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