Methanol → 6-Chloro-2-methyl-4-(1-methylpropyl)amino-5-nitropyridine-3-carboxylic acid, ethyl ester

HRID 1678843Notes

Reaction equation

HRID 1678843 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.[CH:20]([NH2:24])([CH2:22][CH3:23])[CH3:21]>C(N(CC)CC)C>[Cl:11][C:6]1[N:5]=[C:4]([CH3:12])[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:2]([NH:24][CH:20]([CH3:21])[CH2:22][CH3:23])[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 24874Sec-ButylamineHCID 12387594Ethyl 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylate

Product 1

HCID 867355136-Chloro-2-methyl-4-(1-methylpropyl)amino-5-nitropyridine-3-carboxylic 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. methanol. 60 g. of triethylamine are added and the solution is heated at reflux temperature. At this point, 36.5 g. of sec. butylamine are added dropwise. After the addition is completed, 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, 6-chloro-2-methyl-4-(1-methylpropyl)amino-5-nitropyridine-3-carboxylic acid, ethyl ester is recrystallized with methanol, yield: 107 g. (68%); m.p. 33°-35° (methanol).

Workup

  1. temperaturethe solution is heated
  2. temperatureat reflux temperature
  3. additionAfter the addition
  4. temperatureheating
  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, 6-chloro-2-methyl-4-(1-methylpropyl)amino-5-nitropyridine-3-carboxylic acid, ethyl ester is recrystallized with methanol, yield: 107 g

Sources & evidence

ORD record
ord-0b475ffcef1947c881350d48a54662e0
Source dataset
uspto-grants-1978_03
Patent number
US04077955

Reaction notes

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