Triethylamine → 2,N-Dimethyl-N-(3-methyl-4-nitrophenyl)pyridine-4-carboxamide

HRID 1164950Notes

Reaction equation

HRID 1164950 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:11][CH3:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C(N(CC)CC)C.[CH3:20][C:21]1[CH:26]=[C:25]([C:27](Cl)=[O:28])[CH:24]=[CH:23][N:22]=1.S(Cl)(Cl)=O>C(Cl)Cl>[CH3:20][C:21]1[CH:26]=[C:25]([C:27]([N:11]([CH3:12])[C:4]2[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[CH:3]=2)=[O:28])[CH:24]=[CH:23][N:22]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 117884232-Methyl-4-pyridinecarbonyl chlorideHCID 14146034N,3-Dimethyl-4-nitroaniline

Product 1

HCID 198634632,N-Dimethyl-N-(3-methyl-4-nitrophenyl)pyridine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 16.6 g (0.1 mol) of 3,N-dimethyl-4-nitrobenzenamine and 10.2 g (0.1 mol) of triethylamine in mL of methylene chloride cooled to 0° C. under a nitrogen atmosphere add slowly a solution of 15.6 g (0.1 mol) of 2-methylpyridine-4-carbonyl chloride (prepared from the corresponding acid and thionyl chloride) such that the temperature is maintained between 0°-5° C. After the addition is complete, stir the mixture for 6 h and allow to warm slowly to room temperature. Quench the reaction mixture by the addition of 50 mL of water. Separate the layers and wash the organic layer with two 50 mL portions of water, two 50 mL portions of 5% sodium bicarbonate solution and 50 mL of saturated sodium chloride solution. Dry the methylene chloride solution over anhydrous sodium sulfate. Remove the drying agent by filtration and evaporate the solvent to obtain the title compound.

Workup

  1. temperatureis maintained between 0°-5° C
  2. additionAfter the addition
  3. customQuench the reaction mixture
  4. additionby the addition of 50 mL of water
  5. customSeparate the layers
  6. washwash the organic layer with two 50 mL portions of water, two 50 mL portions of 5% sodium bicarbonate solution and 50 mL of saturated sodium chloride solution
  7. dry with materialDry the methylene chloride solution over anhydrous sodium sulfate
  8. customRemove the drying agent
  9. filtrationby filtration
  10. customevaporate the solvent

Sources & evidence

ORD record
ord-9e770a796a1a40d183e65ca7df663776
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

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