Hydrochloric Acid → N-Methyl-N-(3-nitrophenyl)acetamide

HRID 2230940Notes

Reaction equation

HRID 2230940 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[NH:9][C:10](=[O:12])[CH3:11])([O-:5])=[O:4].I[CH3:17].Cl>CN(C)C=O>[CH3:17][N:9]([C:10](=[O:12])[CH3:11])[C:8]1[CH:13]=[CH:14][CH:15]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 312063-Nitroacetanilide

Product 1

HCID 676602N-Methyl-N-(3-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (60% in oil, 5.19 g) in N,N-dimethylformamide (30 ml) was added a solution of 3′-nitroacetanilide (214 mg) in N,N-dimethylformamide (30 ml) at 0° C. The mixture was stirred at room temperature for 30 minutes, then iodomethane (3.59 ml) was added. After 30 minutes, 1N hydrochloric acid was poured into the mixture and extracted with ethyl acetate. The organic solution was washed with water and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give N-methyl-3′-nitroacetanilide (4.64 g).

Workup

  1. waitAfter 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic solution was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resultant solid was collected
  7. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-6dc89c268b964253b1a603add5d998e1
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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