5-nitro-2H,3H-furo(3,2-b)pyridine → 5-Amino-2,3-dihydrofuro[3,2-b]pyridine
Reaction equation
[N+:1]([C:4]1[N:9]=[C:8]2[CH2:10][CH2:11][O:12][C:7]2=[CH:6][CH:5]=1)([O-])=O>CO.[C].[Pd]>[O:12]1[C:7]2[C:8](=[N:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:10][CH2:11]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 5-nitro-2,3-dihydrofuro[3,2-b]pyridine (7.41 g, 44.6 mmol) in methanol (100 mL) was added palladium-carbon powder (500 mg), and the mixture was stirred at room temperature for 16 hr under a hydrogen atmosphere. The catalyst was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by recrystallization (ethyl acetate/hexane) to give the title compound (4.87 g, yield 80%).
Workup
- filtrationThe catalyst was filtered through celite
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by recrystallization (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-1af8b6a0c05d46a184f0d74081951ed0
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273761B2
Reaction notes
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