Hydrochloric Acid → HCID 22768519, compound

HRID 1764494Notes

Reaction equation

HRID 1764494 reaction equation
[O:1]=[C:2]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[C:4](=[O:11])[N:3]1[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14][CH:13]=1.[BH4-].[Na+].Cl>CS(C)=O>[OH:11][CH:4]1[CH:5]2[CH:10]([CH2:9][CH2:8][CH2:7][CH2:6]2)[C:2](=[O:1])[N:3]1[C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 16787059HCID 16787059, compound

Product 1

HCID 22768519HCID 22768519, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

00.2 mole of the 4-(1,3-dioxo-hexahydro-2-isoindolinyl)phenylacetic acid thus obtained was dissolved in 20 ml of dimethyl sulphoxide. The resulting mixture was reduced with 1.14 g (0.03 mole) of sodium borohydride, as described in step (b) of Example 1, and was then poured into ice-water. The mixture was acidified with dilute hydrochloric acid, to precipitate crystals. These crystals were collected by filtration, dried and recrystallized from a mixture of ethanol and petroleum ether, giving 5.0 g (86.2%) of 4-(3-hydroxy-1-oxo-hexahydro-2-isoindolinyl)phenylacetic acid, decomposing at 145° C.

Workup

  1. customto precipitate crystals
  2. filtrationThese crystals were collected by filtration
  3. customdried
  4. customrecrystallized from a mixture of ethanol and petroleum ether

Sources & evidence

ORD record
ord-50e462c2afd14663b1696146f7452c49
Source dataset
uspto-grants-1978_09
Patent number
US04116972

Reaction notes

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