Diethylamine → N,N-Diethyl-2-methyl-5-nitropyridine-3-carboxamide

HRID 972753Notes

Reaction equation

HRID 972753 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15]>C(Cl)(Cl)Cl>[CH2:14]([N:16]([CH2:17][CH3:18])[C:4](=[O:6])[C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[N:10][C:2]=1[CH3:1])[CH3:15]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 2872402-methyl-5-nitronicotinic acid

Product 1

HCID 21405249N,N-Diethyl-2-methyl-5-nitropyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In dry chloroform were dissolved 0.3 g of 2-methyl-5-nitronicotinic acid and 1.5 ml of diethylamine. After addition of 10 g of phosphorous pentaoxide, the mixture was stirred with heating at 55° - 60° C. for 3 hours. After cooling, the chloroform portion was separated and evaporated under reduced pressure. The residue was, after addition of water, neutralized with sodium hydrogen carbonate and extracted with ethyl acetate. The extract was concentrated and purified on a silica gel column to give 0.25 g of a colorless oil.

Workup

  1. additionAfter addition of 10 g of phosphorous pentaoxide
  2. temperaturewith heating at 55° - 60° C. for 3 hours
  3. temperatureAfter cooling
  4. customthe chloroform portion was separated
  5. customevaporated under reduced pressure
  6. additionafter addition of water
  7. extractionextracted with ethyl acetate
  8. concentrationThe extract was concentrated
  9. custompurified on a silica gel column

Sources & evidence

ORD record
ord-d7b2854d4e034bd0b0ed3318118488d7
Source dataset
uspto-grants-1977_10
Patent number
US04053608

Reaction notes

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