2-Amino-6-methoxy-3-nitropyridine → 2,3-Diamino-6-methoxypyridine

HRID 967513Notes

Reaction equation

HRID 967513 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1>CO.C(O)C>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1

Participants

3

Reactant 1

HCID 38524282-Amino-6-methoxy-3-nitropyridine

Product 1

HCID 30239202,3-Diamino-6-methoxypyridine

Reagents, catalysts & solvents 1

HCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

2-Amino-6-methoxy-3-nitropyridine (2.8 g, 16.5 mmol) was dissolved in warm 1:1 methanol/ethanol (200 mL). The solution was cooled, purged with argon, and 10% palladium on carbon was added (0.45 g). Hydrogen was introduced (1 atm) and the reaction stirred until complete. The catalyst was filtered and the solvent evaporated from the filtrate to give the title compound. MS 140 (M+1) 1H NMR (500 MHz, CDCl3) δ 6.93 (d, J=8 Hz, 1H), 6.04 (d, J=8 Hz, 1H), 4.15 (br s, 2H), 3.80 (s, 3H), 3.0 (br s, 2H).

Workup

  1. temperatureThe solution was cooled
  2. custompurged with argon, and 10% palladium on carbon
  3. additionwas added (0.45 g)
  4. additionHydrogen was introduced (1 atm)
  5. filtrationThe catalyst was filtered
  6. customthe solvent evaporated from the filtrate

Sources & evidence

ORD record
ord-035999b95c1c45a68608e50cd307e6a0
Source dataset
uspto-grants-2005_10
Patent number
US06953790B2

Reaction notes

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