6-Methyl-2-nitropyridin-3-ol → 2-Amino-6-methylpyridin-3-ol

HRID 1295193Notes

Reaction equation

HRID 1295193 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N+:8]([O-])=O)[C:5]([OH:11])=[CH:4][CH:3]=1>[Pd].C(OCC)(=O)C>[NH2:8][C:6]1[C:5]([OH:11])=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

4

Reactant 1

HCID 848016-Methyl-2-nitropyridin-3-ol

Product 1

HCID 885002-Amino-6-methylpyridin-3-olYield 98,678.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-methyl-2-nitro-pyridin-3-ol (18.5 g, 0.120 mmol), 10% palladium on activated carbon (1.35 g), and ethyl acetate (240 mL) was hydrogenated for 3 days. The mixture was filtered through Celite and washed with methanol/ethylacetate (5%). The filtrate and washing were combined and concentrated to give the title compound (14.7 g, 99% yield) as a pale brown solid. 1H NMR (DMSO-d6) δ 9.19 (bs, 1H), 6.73 (d, 1H, J=7.6 Hz), 6.12 (d, 1H, J=7.6 Hz), 5.36 (bs, 2H), 2. 15 (s, 3H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with methanol/ethylacetate (5%)
  3. washThe filtrate and washing
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f227358d45f84893be5723830489c9b4
Source dataset
uspto-grants-2007_07
Patent number
US07241789B2

Reaction notes

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