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

HRID 1973107Notes

Reaction equation

HRID 1973107 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9]([Cl:16])=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1Cl)=[O:5])[CH3:2].[CH2:18]([NH2:22])[CH2:19][CH2:20][CH3:21].C(NC1C=C(Cl)NC(C)([N+]([O-])=O)C=1C(OCC)=O)CCC>CO.C(N(CC)CC)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9]([Cl:16])=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[NH:22][CH2:18][CH2:19][CH2:20][CH3:21])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 8007ButylamineHCID 12387594Ethyl 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylateHCID 867342334-Butylamino-6-chloro-2-methyl-2-nitropyridine-3-carboxylic acid, ethyl ester

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×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. The solvent is then removed in vacuo and 500 ml. of benzene are added to the residue. The triethylamine hydrochloride is filtered off and the solvent evaporated. The resulting oil is dissolved in 300 ml. of methanol and yields on cooling 110 g. of 4-butylamino-6-chloro-2-methyl-2-nitropyridine-3-carboxylic acid, ethyl ester (70%), m.p. 33°-35° (methanol).

Workup

  1. temperaturethe solution is heated
  2. temperatureat reflux temperature
  3. customThe solvent is then removed in vacuo and 500 ml
  4. additionof benzene are added to the residue
  5. filtrationThe triethylamine hydrochloride is filtered off
  6. customthe solvent evaporated
  7. dissolutionThe resulting oil is dissolved in 300 ml
  8. customof methanol and yields
  9. temperatureon cooling 110 g

Sources & evidence

ORD record
ord-2c88c7993f9b4719be9f08060b9f5eec
Source dataset
uspto-grants-1976_12
Patent number
US03996233

Reaction notes

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