Acetic Acid → HCID 13257633, compound

HRID 1702119Notes

Reaction equation

HRID 1702119 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:17])[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9]2=[O:18])=[C:4]([F:19])[CH:3]=1.[BH4-].[Na+].C(O)(=O)C>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:16]([OH:17])[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9]2=[O:18])=[C:4]([F:19])[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1859312-(4-Chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-1h-isoindole-1,3(2h)-dioneHCID 4311764Sodium borohydride

Product 1

HCID 13257633HCID 13257633, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 400 ml of ethanol was dissolved 40.0 g of 2-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-1H-isoindol-1,3-dione, and 2.4 g of sodium borohydride was added to the solution with stirring over a 30-minute period, while cooling was effected suitably so as to maintain the reaction temperature at 20° to 30° C. After stirring was further continued at room temperature for 1 hour, the reaction mixture was neutralized with dilute acetic acid and concentrated to about one third of the original volume, followed by cooling. The resulting crystals were collected by filtration, washed with water and dried, thereby affording 36.2 g (yield of 90%) of the subject compound. Recrystallization from ethyl acetate yielded white crystals, m.p. 178°-179° C.

Workup

  1. additionwas added to the solution
  2. temperaturewhile cooling
  3. temperatureto maintain the reaction temperature at 20° to 30° C
  4. stirringAfter stirring
  5. concentrationconcentrated to about one third of the original volume
  6. temperatureby cooling
  7. filtrationThe resulting crystals were collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-a93df3e1e65e471ea2a0a4b4837b7a7f
Source dataset
uspto-grants-1983_04
Patent number
US04380466

Reaction notes

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