Acetic Acid → 4-(3-Hydroxyisoindolin-1-on-2-ylmethylthio)pyridine

HRID 274690Notes

Reaction equation

HRID 274690 reaction equation
[C:1]1(=[O:19])[N:5]([CH2:6][S:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[C:4](=[O:14])[C:3]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:2]12.[BH4-].[Na+].C(O)(=O)C>CO>[OH:19][CH:1]1[C:2]2[C:3](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:4](=[O:14])[N:5]1[CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 190791014-Phthalimidomethylthiopyridine

Product 1

HCID 190791664-(3-Hydroxyisoindolin-1-on-2-ylmethylthio)pyridineYield 58.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 4.01 g (14.8 mmol) of 4-(phthalimidomethylthio)pyridine in 25 ml of methanol, a solution of 1.08 g (29.7 mmol) of sodium borohydride in 20 ml of methanol was added. The mixture was stirred at room temperature for 4 hours. Glacial acetic acid (0.5 ml) was added to quench the reaction, and then the solvent was distilled off. The residue was dissolved in chloroform, washed with water and dried, and the solvent was distilled off. The residue was purified by recrystallization (recrystallization solvent: ethanol) to obtain 2.35 g of the desired compound (yield: 58.3%, yellow crystals).

Workup

  1. customto quench
  2. customthe reaction
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with water
  6. customdried
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by recrystallization (recrystallization solvent: ethanol)

Sources & evidence

ORD record
ord-9834105ee32a4fd687c01ecad1494218
Source dataset
uspto-grants-1995_02
Patent number
US05389658

Reaction notes

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