Acetic Anhydride → Methyl 4-(acetylamino)-2-methoxybenzoate

HRID 1465803Notes

Reaction equation

HRID 1465803 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>C(O)C>[C:14]([NH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1)(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 168705Methyl 4-amino-o-anisate

Product 1

HCID 77720Methyl 4-(acetylamino)-2-methoxybenzoateYield 88.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
62.5 °C

Procedure

To a solution of methyl 4-amino-2-methoxybenzoate (501 mg, 2.77 mmol) in ethanol (8 ml) was added acetic anhydride (0.42 ml, 4.44 mmol, 1.6 eq) and the clear solution heated at 60-65° C. for 2 h. After cooling to room temperature the solvent was removed by rotary evaporator and the residue treated with water (10 ml) and saturated sodium bicarbonate solution (10 ml) before extracting with ethyl acetate (20 ml, 2×10 ml). The combined ethyl acetate extract was washed with water, then brine, dried (MgSO4) and evaporated to give methyl 4-acetamido-2-methoxybenzoate (545 mg, 88%) as a white solid.

Workup

  1. temperatureAfter cooling to room temperature the solvent
  2. customwas removed by rotary evaporator
  3. additionthe residue treated with water (10 ml) and saturated sodium bicarbonate solution (10 ml)
  4. extractionbefore extracting with ethyl acetate (20 ml, 2×10 ml)
  5. extractionThe combined ethyl acetate extract
  6. washwas washed with water
  7. dry with materialbrine, dried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-9f2dc9f704f04c0d8e3b7a9b7320a5c7
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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