Furo[3,2-b]pyridine, 2,3-dihydro-5-nitro- → 5-Amino-2,3-dihydrofuro[3,2-b]pyridine

HRID 2389921Notes

Reaction equation

HRID 2389921 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]1

Participants

4

Reactant 1

HCID 10654607Furo[3,2-b]pyridine, 2,3-dihydro-5-nitro-

Product 1

HCID 552820545-Amino-2,3-dihydrofuro[3,2-b]pyridineYield 80.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

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

  1. filtrationThe catalyst was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. 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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