2-Cyclopentyloxy-5-nitro-pyridine → 6-(Cyclopentyloxy)pyridin-3-amine

HRID 657246Notes

Reaction equation

HRID 657246 reaction equation
[CH:1]1([O:6][C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([O:6][C:7]2[N:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 150095792-Cyclopentyloxy-5-nitro-pyridine

Product 1

HCID 167909726-(Cyclopentyloxy)pyridin-3-amineYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-cyclopentyloxy-5-nitro-pyridine (0.3099 g, 1.49 mmol), in MeOH (2 mL) was added 10% Pd/C (90 mg). The solution was degassed and was kept stirring under hydrogen atmosphere for overnight. It was filtered through a pad of celite and the filtrate was evaporated to afford the desired product as a brown oil (248 mg, 94% yield). 1H-NMR (300 MHz, CDCl3): δ 7.69 (d, 1H), 7.04 (m, 1H), 6.56 (d, 1H), 5.25 (m, 1H), 1.93 (m, 2H), 1.78 (m, 4H), 1.60 (m, 2H). LC/MS (ESI) calcd for C10H14N2O 178.23, found [M+41+1]+ 220.0.

Workup

  1. customThe solution was degassed
  2. filtrationIt was filtered through a pad of celite
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-a3de80b71d4542f4b69d32b6a6988fd7
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

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