Methanol → 4-Butylamino-6-chloro-2-methyl-5-nitronicotinic acid ethyl ester

HRID 1658522Notes

Reaction equation

HRID 1658522 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[C:4]([CH3:12])[C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].CO.[CH2:20]([NH2:24])[CH2:21][CH2:22][CH3:23]>C(N(CC)CC)C>[CH2:20]([NH:24][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[C:4]([CH3:12])[C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 8007ButylamineHCID 12387594Ethyl 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

139.5 g. of 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylic acid, ethyl ester (0.5 mol.) are dissolved in about 500 ml. of methanol. 60 g. of triethylamine are added and the solution is heated at reflux temperature. At this point, 36.5 g. n-butylamine are added dropwise. After the addition is completed, the heating is continued for 10 minutes. The solvent is then removed in vacuo and 500 ml. of ethyl acetate are added to the residue. The triethylamine hydrochloride is filtered off and the solvent evaporated. The resulting yellow oil, 4-butylamino-6-chloro -2methyl-5nitropyridine-3-carboxylic acid, ethyl ester is crystallized with 300 ml. of methanol, yield 110 g. (70%); m.p. 33°-35° (methanol).

Workup

  1. temperaturethe solution is heated
  2. temperatureat reflux temperature
  3. additionAfter the addition
  4. customThe solvent is then removed in vacuo and 500 ml
  5. additionof ethyl acetate are added to the residue
  6. filtrationThe triethylamine hydrochloride is filtered off
  7. customthe solvent evaporated
  8. customThe resulting yellow oil, 4-butylamino-6-chloro -2methyl-5nitropyridine-3-carboxylic acid, ethyl ester is crystallized with 300 ml

Sources & evidence

ORD record
ord-c945dab864804979912539377b63bc1b
Source dataset
uspto-grants-1976_06
Patent number
US03965108

Reaction notes

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