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

HRID 470117Notes

Reaction equation

HRID 470117 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-5a6f0f4463294462ac92a882864cb089
Source dataset
uspto-grants-2014_01
Patent number
US08629162B2

Reaction notes

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