6-Chloro-4[(1,1-dimethylethyl)amino]-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester → 4-Amino-6-chloro-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester

HRID 2397569Notes

Reaction equation

HRID 2397569 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:21])=[N:8][C:9]([Cl:20])=[C:10]([N+:17]([O-:19])=[O:18])[C:11]=1[NH:12]C(C)(C)C)=[O:5])[CH3:2]>CO>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:21])=[N:8][C:9]([Cl:20])=[C:10]([N+:17]([O-:19])=[O:18])[C:11]=1[NH2:12])=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 543302406-Chloro-4[(1,1-dimethylethyl)amino]-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester

Product 1

HCID 544502124-Amino-6-chloro-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

31.6 g. of 6-chloro-4[(1,1-dimethylethyl)amino]-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester (0.1 mol.) are heated with stirring at 250°-260° for 5 minutes. The dark oil is cooled to room temperature and 50 ml. of methyl alcohol are added. 18.2 g. of 4-amino-6-chloro-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester crystallize on cooling (70%), m.p. 89-91° (methanol).

Workup

  1. customof 4-amino-6-chloro-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester crystallize
  2. temperatureon cooling (70%), m.p. 89-91° (methanol)

Sources & evidence

ORD record
ord-63c2eb70f10c41e2b53759a70cec8858
Source dataset
uspto-grants-1977_05
Patent number
US04022779

Reaction notes

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