Methylhydrazine → 4-Chloro-6-(1-methyl)hydrazino-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester

HRID 1973112Notes

Reaction equation

HRID 1973112 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[N:5]=[C:4]([CH3:12])[C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH3:18][NH:19][NH2:20]>CO>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([N:19]([CH3:18])[NH2:20])[N:5]=[C:4]([CH3:12])[C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 12387594Ethyl 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylate

Product 1

HCID 123876134-Chloro-6-(1-methyl)hydrazino-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

27.9 g. of 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylic acid, ethyl ester (0.1 Mol.) are dissolved in about 100 ml. of methanol. At 50°, 9.2 g. of methylhydrazine are dropped in and the mixture is stirred for 30 minutes. On cooling, 4-chloro-6-(1-methyl)hydrazino-2-methyl-5-nitropyridine-3-carboxylic acid, ethyl ester precipitates, yield: 18 g. (62.2%), m.p. 159°-161° (methanol).

Workup

  1. customAt 50°
  2. temperatureOn cooling
  3. custom4-chloro-6-(1-methyl)hydrazino-2-methyl-5-nitropyridine-3-carboxylic acid, ethyl ester precipitates

Sources & evidence

ORD record
ord-8b97c84487b74d6ca1546888800f2b56
Source dataset
uspto-grants-1976_12
Patent number
US03996233

Reaction notes

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