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

HRID 863986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 863986
[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

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 190791014-Phthalimidomethylthiopyridine

Produkt 1

HCID 190791664-(3-Hydroxyisoindolin-1-on-2-ylmethylthio)pyridineAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-42aa2cd0817549c48e1b04f8db87f2e4
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05561147

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