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

HRID 2060054Notes

Reaction equation

HRID 2060054 reaction equation
[OH:1][C:2]1[C:3]([N+:9]([O-])=O)=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1>[Pd].C(O)C>[NH2:9][C:3]1[C:2]([OH:1])=[CH:7][CH:6]=[C:5]([CH3:8])[N:4]=1

Participants

4

Reactant 1

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

Product 1

HCID 885002-Amino-6-methylpyridin-3-olYield 81.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-hydroxy-6-methyl-2-nitropyridine (4.2 g, 27 mmol) and 10% palladium on carbon (0.25 g, 0.24 mmol) in ethanol (75 mL) was stirred at rt under an atmosphere of hydrogen for 24 hr. The catalyst was removed by filtration through celite and the filtrate concentrated to dryness under vacuum. The residue was subjected to chromatography on silica gel using Biotage SP1 employing a 40+M cartridge and eluting with MeOH/DCM 10% 2 CV, 10-35% in 10 CV, 35% 2 CV. The purified product 2-amino-6-methyl-3-pyridinol (D145, 2.72 g, 80%) was isolated as pale brown solid.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. concentrationthe filtrate concentrated to dryness under vacuum
  3. washeluting with MeOH/DCM 10% 2 CV, 10-35% in 10 CV, 35% 2 CV

Sources & evidence

ORD record
ord-9f4bb7ba1bb948d982c2279e6e1a58e4
Source dataset
uspto-grants-2012_10
Patent number
US08278328B2

Reaction notes

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