2-Isopropyl-5-nitropyridine → 6-(Propan-2-yl)pyridin-3-amine

HRID 423907Notes

Reaction equation

HRID 423907 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][N:5]=1)([CH3:3])[CH3:2]>CO.[Ni]>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 450963212-Isopropyl-5-nitropyridine

Product 1

HCID 178542886-(Propan-2-yl)pyridin-3-amineYield 52%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

2-Isopropyl-5-nitro-pyridine (1.30 g, 7.82 mmol) was dissolved in methyl alcohol (20 mL), and Raney Ni (0.25 g) was added. The mixture was stirred under H2 (1 atm) at room temperature for 2 h. The catalyst was filtered off, and the filtrate was concentrated under vacuum to give 2-isopropyl-5-amino-pyridine (E-9) (0.55 g, 52%). 1H NMR (CDCl3) δ 8.05 (s, 1 H), 6.93-6.99 (m, 2 H), 3.47 (br s, 2 H), 2.92-3.02 (m, 1 H), 1.24-1.26 (m, 6 H). ESI-MS 137.2 m/z (MH+).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-d497a648cf5e44ddaea4ca283d71d26e
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Reaction notes

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