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

HRID 1768182Notes

Reaction equation

HRID 1768182 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-dfd2849e1f6944538e202de87263bb9c
Source dataset
uspto-grants-2007_06
Patent number
US07235545B2

Reaction notes

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