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

HRID 505390Notes

Reaction equation

HRID 505390 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.[NH3:13]>CN(C)C=O.O>[CH3:12][O:11][C:4]1[N:3]=[C:2]([NH2:13])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 27950292-Chloro-6-methoxy-3-nitropyridine

Product 1

HCID 38524282-Amino-6-methoxy-3-nitropyridineYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-6-methoxy-3-nitropyridine (25.3 g, 0.134 mol) and a concentrated aqueous ammonia solution (70 ml) in N,N-dimethylformamide (200 ml) was stirred at 70° C. for 4 hours and 15 minutes. The reaction mixture was cooled to room temperature and then diluted with water. The resulted precipitate was collected by filtration to yield the title compound (16.8 g, 99.2 mmol, 74.0%) as a yellow solid.

Workup

  1. filtrationThe resulted precipitate was collected by filtration

Sources & evidence

ORD record
ord-1b169461ff614a7e85cff688aba58dac
Source dataset
uspto-grants-2010_08
Patent number
US07781452B2

Reaction notes

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