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

HRID 1415134Notes

Reaction equation

HRID 1415134 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9](Cl)=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[Cl:12])=[O:5])[CH3:2].CO.O.[CH2:21]([NH:23][NH2:24])[CH3:22]>C(N(CC)CC)C>[Cl:12][C:11]1[C:10]([N+:13]([O-:15])=[O:14])=[C:9]([NH:24][NH:23][CH2:21][CH3:22])[N:8]=[C:7]([CH3:17])[C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 29062EthylhydrazineHCID 12387594Ethyl 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylate

Product 1

HCID 867344174-Chloro-6-(1-ethyl)hydrazino-2-methyl-5-nitropyridine-3-carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

27.9 g. of 4,6-Dichloro-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester (0.2 mol.) are dissolved in about 100 ml. of methanol and 20 ml. of water. 15 g. of triethylamine are added and at 25°-30° 4.5 g. ethyl hydrazine are dropped in with stirring. After the addition is complete, stirring is continued for 1 additional hour. On cooling, 4-chloro-6-(1-ethyl)hydrazino-2-methyl-5-nitropyridine-3-carboxylic acid, ethyl ester precipitates, yield 19.7 g. (65%) m.p. 117°-120°.

Workup

  1. additionAfter the addition
  2. stirringstirring
  3. temperatureOn cooling
  4. custom4-chloro-6-(1-ethyl)hydrazino-2-methyl-5-nitropyridine-3-carboxylic acid, ethyl ester precipitates

Sources & evidence

ORD record
ord-c97ae0e29fec493d9231b8ce306a9ac2
Source dataset
uspto-grants-1977_01
Patent number
US04003908

Reaction notes

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