4-Methyl-3-nitrobenzoic acid → HCID 799022, compound

HRID 869216Notes

Reaction equation

HRID 869216 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].S(Cl)(Cl)=O.C1COCC1.[CH2:23]([NH:25][CH2:26][CH3:27])[CH3:24]>O>[CH2:23]([N:25]([CH2:26][CH3:27])[C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1)[CH3:24]

Participants

6

Reactant 4

HCID 73194-Methyl-3-nitrobenzoic acidHCID 8021DiethylamineHCID 8028TetrahydrofuranHCID 24386Thionyl Chloride

Product 1

HCID 799022HCID 799022, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-methyl-3-nitrobenzoic acid (1.97 g) and thionyl chloride (6 mL) was heated under reflux for 18 hours. The reaction liquid was concentrated under reduced pressure, followed by an azeotropic process with toluene to give a red-brown oil. To a mixture of the red-brown oil and THF (25 mL), diethylamine (2.6 mL) was added under ice cooling and stirred at room temperature for 5 hours. The reaction liquid was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give N,N-diethyl-4-methyl-3-nitrobenzamide (2.61 g) as a brown oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customThe reaction liquid
  4. concentrationwas concentrated under reduced pressure
  5. customto give a red-brown oil
  6. additionwas added under ice cooling
  7. customThe reaction liquid
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed with saturated aqueous sodium chloride
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-25e8a5f06dac4f3e99f6ffbe463b4f8c
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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