Sodium borohydride → 4-[3-(2-Hydroxymethylbenzoyl)aminopropylthio]pyridine

HRID 6156Notes

Reaction equation

HRID 6156 reaction equation
[C:1]1(=[O:21])[N:5]([CH2:6][CH2:7][CH2:8][S:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[C:4](=[O:16])[C:3]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:2]12.[BH4-].[Na+]>C(O)C>[OH:21][CH2:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=1)=[O:16]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 190791181H-Isoindole-1,3(2H)-dione, 2-[3-(4-pyridinylthio)propyl]-

Product 1

HCID 190791424-[3-(2-Hydroxymethylbenzoyl)aminopropylthio]pyridineYield 78.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5.97 g (20.0 mmol) of 4-(3-phthalimidopropylthio)pyridine in 300 ml of ethanol, 7.57 g (200 mmol) of sodium borohydride was added, and stirred at room temperature for 24 hours. The solvent was distilled off and saturated saline was added to the residue. The mixture was extracted with chloroform and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethanol/ethyl acetate =1:10) to give 4.73 g of the desired compound (78.2% yield, colorless crystals), mp. 110°-111° C.

Workup

  1. distillationThe solvent was distilled off
  2. additionsaturated saline was added to the residue
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: ethanol/ethyl acetate =1:10)

Sources & evidence

ORD record
ord-f7c946d278a44fe28f799ef9783e5d4b
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Reaction notes

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