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

HRID 2397568Notes

Reaction equation

HRID 2397568 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9]([Cl:16])=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1Cl)=[O:5])[CH3:2].[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19]>C(N(CC)CC)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9]([Cl:16])=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[NH:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 12387594Ethyl 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

55.8 g. of 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester (0.2 mol.) are dissolved in 300 ml. of alcohol and 25 g. of triethylamine. At reflux temperature, 14.6 g. of tert. butylamine are slowly added dropwise and the mixture is heated with stirring for an additional 30 minutes. The solvent is distilled off in vacuo and the residue is dissolved in benzene. The precipitated triethylamine hydrochloride is filtered off and the benzene layer is evaporated to dryness. The remaining oil, 6-chloro-4-[(1,1-dimethylethyl)amino]-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester crystallizes with methanol, yield 38.4 g. (61%), m.p. 40°-43°.

Workup

  1. temperatureAt reflux temperature, 14.6 g
  2. temperaturethe mixture is heated
  3. distillationThe solvent is distilled off in vacuo
  4. dissolutionthe residue is dissolved in benzene
  5. filtrationThe precipitated triethylamine hydrochloride is filtered off
  6. customthe benzene layer is evaporated to dryness
  7. customThe remaining oil, 6-chloro-4-[(1,1-dimethylethyl)amino]-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester crystallizes with methanol, yield 38.4 g

Sources & evidence

ORD record
ord-3d04e181143340a39321c8cda554ee6a
Source dataset
uspto-grants-1977_05
Patent number
US04022779

Reaction notes

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