Ammonia → 2-Amino-6-methoxy-3-nitropyridine

HRID 1943173Notes

Reaction equation

HRID 1943173 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1.CO.[NH3:15]>>[CH3:12][O:11][C:4]1[N:3]=[C:2]([NH2:15])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 222Ammonia2×HCID 887MethanolHCID 27950292-Chloro-6-methoxy-3-nitropyridine

Product 1

HCID 38524282-Amino-6-methoxy-3-nitropyridineYield 84%

Procedure

A solution/suspension of 2-chloro-6-(methyloxy)-3-nitropyridine (65.7 g, 348 mmol) in 2M ammonia in methanol (500 ml, 1000 mmol) and aqueous ammonia (500 ml, 348 mmol) was stirred at 65° C. for 18 h. The reaction was cooled down and the solid filtered off and washed with water (2×100 ml). The solid was dried in the vacuum oven at 40° C. overnight to afford the product as a bright yellow solid (52.14 g, 84% purity by NMR, 74%).

Workup

  1. temperatureThe reaction was cooled down
  2. filtrationthe solid filtered off
  3. washwashed with water (2×100 ml)
  4. customThe solid was dried in the vacuum oven at 40° C. overnight

Sources & evidence

ORD record
ord-5eed3e6951064788aba36bf9dc79cf51
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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