Hexahydrophthalic anhydride, cis- → HCID 20384700, compound

HRID 47010

Reaction equation

HRID 47010 reaction equation
[C@@H:1]12[C:10](=[O:11])[O:9][C:7](=O)[C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[NH2:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=1[F:21]>C(O)(=O)C>[O:9]=[C:7]1[CH:2]2[CH:1]([CH2:6][CH2:5][CH2:4][CH2:3]2)[C:10](=[O:11])[N:12]1[C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=1[F:21]

Participants

4

Reactant 2

HCID 641660Hexahydrophthalic anhydride, cis-HCID 27564314-Amino-3-fluorobenzonitrile

Product 1

HCID 20384700HCID 20384700, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5 parts of cis-1,2-cyclohexane dicarboxylic anhydride in 75 parts of glacial acetic acid was added 4.8 parts of 4-amino-3-fluorobenzonitrile in one portion. The mixture was refluxed for 4 hours, poured over 200 parts of ice and filtered. The crude crystalline product was recrystallized from methanol to yield 4.4 parts of beige 4-(1,3-dioxo-2,3,3a,4,5,6,7,7a-octahydro-1H-isoindol-2-yl)-3-fluorobenzonitrile melting 120°-123°.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. additionpoured over 200 parts of ice
  3. filtrationfiltered
  4. customThe crude crystalline product was recrystallized from methanol

Sources & evidence

ORD record
ord-695eb91dec3049ec9dfb2355e89b357a
Source dataset
uspto-grants-1979_11
Patent number
US04175948

Linked notes

Loading…