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

HRID 1606536Notes

Reaction equation

HRID 1606536 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. of n-butylamine are added dropwise. After the addition is completed, the heating is continued for ten 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 is crystallized with 300 ml. of methanol to give 4-butylamino-6-chloro-2-methyl-5-nitropyridine-3-carboxylic acid, ethyl ester, yield 110 g. (70%), m.p. 33°-35° (methanol).

Workup

  1. temperaturethe solution is heated
  2. temperatureat reflux temperature
  3. additionAfter the addition
  4. waitthe heating is continued for ten minutes
  5. customThe solvent is then removed in vacuo and 500 ml
  6. additionof ethyl acetate are added to the residue
  7. filtrationThe triethylamine hydrochloride is filtered off
  8. customthe solvent evaporated
  9. customThe resulting yellow oil is crystallized with 300 ml

Sources & evidence

ORD record
ord-d62230ae87d94754bcf8e9b9e4fa12bd
Source dataset
uspto-grants-1976_04
Patent number
US03953461

Reaction notes

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