Dimethylamine → N,N-dimethyl-5-nitropyridin-2-amine

HRID 1728601Notes

Reaction equation

HRID 1728601 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][NH:12][CH3:13]>>[CH3:11][N:12]([CH3:13])[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 75707N,N-dimethyl-5-nitropyridin-2-amineYield 98%

Procedure

2-Chloro-5-nitropyridine (1.58 g, 10 mM) was treated with a 33% w/w solution of dimethylamine in methylated spirit (18 ml, 100 mM). An exothermic reaction ensued, with formation of a yellow solid. After 0.5 h the solid was filtered off. The filtrate was evaporated and the residue was combined with the yellow solid, and all material was dissolved in dichloromethane. This solution was washed with water and brine, dried and evaporated, to give the title compound (1.64 g; 98%), m.p. 146°-149° C.

Workup

  1. customAn exothermic reaction
  2. filtrationAfter 0.5 h the solid was filtered off
  3. customThe filtrate was evaporated
  4. dissolutionall material was dissolved in dichloromethane
  5. washThis solution was washed with water and brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-7f2f995dee8940cdacd64d4048e22267
Source dataset
uspto-grants-1994_07
Patent number
US05328922

Reaction notes

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