3-Methoxy-2-nitropyridine → 2-Amino-3-methoxypyridine

HRID 710932Notes

Reaction equation

HRID 710932 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:9]([O-])=O)=[N:5][CH:6]=[CH:7][CH:8]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 5560633-Methoxy-2-nitropyridine

Product 1

HCID 99203842-Amino-3-methoxypyridineYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 3-methoxy-2-nitropyridin (30 g, 194.8 mmol) and 10% Pd/C (10 g) in ethanol (1 L) was hydrogenated in a par hydrogenator (H2, 40 psi pressure) at RT for 4 hours. The reaction mixture was filtered through celite and the filtrate was concentrated to afford the title compound (22 g, 91%, brown solid). 1H NMR (400 MHz, CDCl3): δ=7.66 (d, J=5.2 Hz; 1H), 6.91 (d, J=7.6 Hz, 1H), 6.63-6.60 (m, 1H), 4.65 (br, 2H), 3.84 (s, 3H) ppm.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e32e3ca326f644b1bcccd6f89c60498d
Source dataset
uspto-grants-2015_11
Patent number
US09181248B2

Reaction notes

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