Acetic Anhydride → Ethyl 4-(acetylamino)-3-ethoxybenzoate

HRID 402778

Reaction equation

HRID 402778 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][CH2:14][CH3:15].[C:16](OC(=O)C)(=[O:18])[CH3:17]>CN(C)C1C=CN=CC=1.CCOC(C)=O>[C:16]([NH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][CH2:14][CH3:15])(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 825957Benzoic acid, 4-amino-3-ethoxy-, ethyl ester

Product 1

HCID 66765155Ethyl 4-(acetylamino)-3-ethoxybenzoateYield 70.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a 100 mL round bottom flask were added ethyl 4-amino-3-ethoxybenzoate (1.3 g, 6.2 mmol), TEA (2.6 mL, 18.6 mmol), N,N-dimethylpyridin-4-amine (catalytic), acetic anhydride (0.88 mL, 9.3 mmol) and EtOAc (20 mL). The reaction mixture was stirred at ambient temperature for 3 hours and was then diluted with EtOAc (20 mL) and washed with 5% KOH (50 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified on a silica gel column eluting with a gradient of EtOAc/hexanes to give the title intermediate (1.1 g) as a pale yellow solid.

Workup

  1. washwashed with 5% KOH (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified on a silica gel column
  6. washeluting with a gradient of EtOAc/hexanes

Sources & evidence

ORD record
ord-027a69ab6c71446ba26610b17c2ed133
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Linked notes

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