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

HRID 1287232Notes

Reaction equation

HRID 1287232 reaction equation
[CH2:1]([NH:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10](Cl)[N:9]=[C:8]([CH3:16])[C:7]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:2][CH2:3][CH3:4].[NH3:22]>CO>[NH2:22][C:10]1[N:9]=[C:8]([CH3:16])[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[C:11]=1[N+:12]([O-:14])=[O:13]

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-nitropyridine-3-carboxylic acid, ethyl ester (0.5 Mol.) dissolved in 500 ml. of methanol are heated with 300 ml. of aqueous ammonia (30%) in an autoclave 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-0716dd700925473e8c7605f66456f495
Source dataset
uspto-grants-1976_10
Patent number
US03984412

Reaction notes

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