Ammonia → 6-Amino-4-butylamino-2-methyl-5-nitronicotinic acid ethyl ester

HRID 1973114Notes

Reaction equation

HRID 1973114 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[C:10]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])=[C:9]([N+:16]([O-:18])=[O:17])[C:8](Cl)=[N:7][C:6]=1[CH3:20])[CH3:2].[NH3:22]>CO>[NH2:22][C:8]1[N:7]=[C:6]([CH3:20])[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:21])=[C:10]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:9]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 123875984-Butylamino-6-chloro-2-methyl-5-nitronicotinic acid ethyl ester

Product 1

HCID 123876046-Amino-4-butylamino-2-methyl-5-nitronicotinic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

177.9 g. of 4-butylamino-6-chloro-2-methyl-5-nitronicotinic acid ethyl ester (0.5 Mol.) and 500 ml. of methanol are heated in an autoclave together with 300 ml. of aqueous ammonia (30%) at about 60° for 10 hours. After this time, the solvent is distilled off and the residual 6-amino-4-butylamino-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester is recrystallized from methanol, yield: 135 g., m.p. 98°-99°.

Workup

  1. distillationAfter this time, the solvent is distilled off
  2. customthe residual 6-amino-4-butylamino-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester is recrystallized from methanol, yield: 135 g

Sources & evidence

ORD record
ord-203bbecd48f24adf8230f47b844019b0
Source dataset
uspto-grants-1976_12
Patent number
US03996233

Reaction notes

Loading…