Diethylamine → HCID 20321213, compound

HRID 973061Notes

Reaction equation

HRID 973061 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C(Cl)(Cl)Cl>[CH2:14]([N:16]([CH2:17][CH3:18])[C:7](=[O:9])[C:6]1[CH:10]=[C:2]([CH3:1])[N:3]=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=1)[CH3:15]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 14812Phosphorus oxide (P4O10)HCID 124040282-Methyl-6-nitropyridine-4-carboxylic acid

Product 1

HCID 20321213HCID 20321213, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 1.0 g. of 6-methyl-2-nitroisonicotinic acid, 20 ml. of chloroform and 3 ml. of diethylamine was added 7.0 g. of phosphorus pentoxide with stirring. The resulting mixture was refluxed for 1 hour. After cooling, the chloroform layer was separated and poured into 20 ml. of water. The resulting mixture was neutralized with sodium hydrogencarbonate and the chloroform layer was separated, dried ever anhydrous sodium sulfate and the chloroform was distilled off in vacuo. The residual oil was gradually crystallized and then recrystallized from ethyl acetate - n-hexane to give 0.6 g. of the desired product.

Workup

  1. additionTo a mixture of 1.0 g
  2. temperatureThe resulting mixture was refluxed for 1 hour
  3. temperatureAfter cooling
  4. customthe chloroform layer was separated
  5. additionpoured into 20 ml
  6. customthe chloroform layer was separated
  7. dry with materialdried ever anhydrous sodium sulfate
  8. distillationthe chloroform was distilled off in vacuo
  9. customThe residual oil was gradually crystallized
  10. customrecrystallized from ethyl acetate - n-hexane
  11. customto give 0.6 g

Sources & evidence

ORD record
ord-9509ca699a554d178bdc1d57ba2a9928
Source dataset
uspto-grants-1977_10
Patent number
US04054663

Reaction notes

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