Acetate → 4-[acetyl(methyl)amino]benzoic acid

HRID 1757451Notes

Reaction equation

HRID 1757451 reaction equation
[CH3:1][NH:2][C:3]1[CH:11]=[CH:10]C(C(O)=O)=[CH:5][CH:4]=1.C([O:15][C:16](=[O:18])[CH3:17])(=O)C.[C:19]([O-])(=[O:21])[CH3:20]>N1C=CC=CC=1>[C:19]([N:2]([C:3]1[CH:4]=[CH:5][C:17]([C:16]([OH:15])=[O:18])=[CH:10][CH:11]=1)[CH3:1])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 175AcetateHCID 7918Acetic AnhydrideHCID 663454-(Methylamino)benzoic acid

Product 1

HCID 2834714-[acetyl(methyl)amino]benzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-methyl-4-aminobenzoic acid (2.0 g, 13.2 mmol) in anhydrous pyridine (13.2 mL) was added acetic anhydride (1.4 mL, 14.5 mmol). The reaction was stirred at ambient temperature until TLC indicatedcomplete reaction (~22 hours). The resultant solution was poured intoethyl acetate and the organic phase was washed (3×, 10% HCl; 1×, water; 1×, brine), dried (MgSO4), filtered and concentrated in vacuo to provide the amide as a colorless solid. Recrystallization (ethyl acetate/hexane) afforded 4-(N-acetyl-N-methylamino)benzoic acid (2.15 g, 84.0%). 1H NMR (300 MHz, CDCl3) d 8.18 (2H, br d, J=8.5 Hz), 7.33 (2H, br d, J=8.5 Hz), 3.33 (3H, s), 2.0 (3H, br s). MS m/e 194 (M+H)+, 211 (M+NH4)+.

Workup

  1. washthe organic phase was washed (3×, 10% HCl; 1×, water; 1×, brine)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1db617975f844eeabfd9bff0e0578068
Source dataset
uspto-grants-1995_08
Patent number
US05446062

Reaction notes

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