Acetic Acid → HCID 13257633, compound

HRID 647403Notes

Reaction equation

HRID 647403 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 to maintain the reaction temperature at 20° to 30° C. After stirring was continued at room temperature for one hour, the reaction mixture was neutralized with dilute acetic acid and concentrated to about one third of the original volume. Upon cooling, there resulted crystals, which 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. temperatureUpon cooling
  7. customthere resulted crystals, which
  8. filtrationwere collected by filtration
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-c35e4c79845c4ccbb76e9d7e609446bb
Source dataset
uspto-grants-1983_10
Patent number
US04409018

Reaction notes

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