N-Ethylbenzylamine → HCID 68133424, compound

HRID 1973110Notes

Reaction equation

HRID 1973110 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9](Cl)=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[Cl:12])=[O:5])[CH3:2].[CH2:18]([NH:25][CH2:26][CH3:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(N(CC)CC)C>[Cl:12][C:11]1[C:10]([N+:13]([O-:15])=[O:14])=[C:9]([N:25]([CH2:26][CH3:27])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:8]=[C:7]([CH3:17])[C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

4

Reactant 2

HCID 84352N-EthylbenzylamineHCID 12387594Ethyl 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylate

Product 1

HCID 68133424HCID 68133424, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

279 g. of 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylic acid ethyl ester are dissolved in 700 ml. of alcohol. 150 g. of triethylamine are added and at reflux temperature 135 g. of benzyl(ethyl)amine are slowly dropped in. After the addition is completed, the heating is continued for another hour. After this time, the solvent is removed in vacuo, 300 ml. of water are added and the mixture extracted three times with 200 ml. portions of ether. The organic layers are combined, dried with calcium chloride and the solvent is distilled off. The resulting oil is distilled in vacuo, b.p.0.05 210°-220°. The crude product is dissolved in 300 ml. of ether and cooled to about -50°. After 24 hours, the isomeric compound 6-chloro-4-[ethyl(phenylmethyl)amino]-2-methyl-5-nitro-3-pyridinecarboxylic acid ethyl ester precipitates, is filtered off and the filtrate evaporated to dryness. The resulting 4-chloro-6-[ethyl(phenylmethyl)amino]-2-methyl-5-nitro-3-pyridinecarboxylic acid, yield 215 g. (56%) is used without further purification.

Workup

  1. temperatureat reflux temperature 135 g
  2. additionAfter the addition
  3. waitthe heating is continued for another hour
  4. customAfter this time, the solvent is removed in vacuo, 300 ml
  5. additionof water are added
  6. extractionthe mixture extracted three times with 200 ml
  7. dry with materialdried with calcium chloride
  8. distillationthe solvent is distilled off
  9. distillationThe resulting oil is distilled in vacuo, b.p.0.05 210°-220°
  10. dissolutionThe crude product is dissolved in 300 ml
  11. temperatureof ether and cooled to about -50°
  12. customthe isomeric compound 6-chloro-4-[ethyl(phenylmethyl)amino]-2-methyl-5-nitro-3-pyridinecarboxylic acid ethyl ester precipitates
  13. filtrationis filtered off
  14. customthe filtrate evaporated to dryness
  15. custom(56%) is used without further purification

Sources & evidence

ORD record
ord-76c3496e8f2e4fed8a4278fe39e5b5be
Source dataset
uspto-grants-1976_12
Patent number
US03996233

Reaction notes

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