Reaktion #6273

Reaktionsgleichung

water

ammonia

4-[(3-hydroxyisoindolin-1-on-2-yl)methylthio]pyridine

sodium borohydride

→

desired product

Ausbeute 54.6%

4-[(isoindolin-1-on-2-yl)methylthio]pyridine

Ausbeute 54.6%

Lösungsmittel

trifluoroacetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Extraktionfollowed by extraction with methylene chloride
3. 3
   TrocknenThe extract was dried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONthe solvent was distilled off
5. 5
   SonstigeThe residue was purified by recrystallization (solvent: ethyl acetate)

Vorschrift

To a solution of 681 mg (2.5 mmol) of 4-[(3-hydroxyisoindolin-1-on-2-yl)methylthio]pyridine in 6 ml of trifluoroacetic acid, 0.30 g (7.93 mmol) of sodium borohydride was added in small portions, and the mixture was stirred for 15 minutes. The reaction mixture was poured into cold water and aqueous ammonia was added to make the mixture basic, followed by extraction with methylene chloride. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was purified by recrystallization (solvent: ethyl acetate) to give 350 mg of the desired product (54.6% yield, colorless columns), mp. 131°-132° C.

Quelle