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

HRID 1727649Notes

Reaction equation

HRID 1727649 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 vaccum to give 2-isopropyl-5-amino-pyridine (E-9) (0.55 g, 52%). 1H NMR (CDCl3) δ 8.05 (s, 1H), 6.93-6.99 (m, 2H), 3.47 (br s, 2H), 2.92-3.02 (m, 1H), 1.24-1.26 (m, 6H). ESI-MS 137.2 m/z (MH+).

Workup

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

Sources & evidence

ORD record
ord-7fdad5f366e844b5b4ad73059162b415
Source dataset
uspto-grants-2009_02
Patent number
US07495103B2

Reaction notes

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