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

HRID 367086Notes

Reaction equation

HRID 367086 reaction equation
[OH:1][C:2]1[C:3]([N+:9]([O-])=O)=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1>CCO.[Pd]>[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 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Hydroxy-6-methyl-2-nitropyridine from Example 117a (10.5 g, 68 mmole) was combined with 10% Pd/C (100 mg) in EtOH (100 mL), and the mixture was stirred under a H2 atmosphere for 16 hours. The mixture was filtered and concentrated to yield 8.40 g (99%) of the title compound. mp 141-145° C. 1H NMR (DMSO-d6, 300 MHz) δ: 2.14 (s, 3H), 6.22 (d, J=7.5 Hz, 1H), 6.71 (d J=7.5 Hz, 1H). MS (DCI/NH3) m/e 125 (M+H)+, 142 (M+NH4)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-2743861531f1415693425b0ef00544c9
Source dataset
uspto-grants-2000_10
Patent number
US06133253

Reaction notes

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