Pyridine → 4-(Acetylamino)-2,5-dimethylphenyl acetate

HRID 1269821Notes

Reaction equation

HRID 1269821 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:14][C:15]1[CH:20]=[C:19]([NH2:21])[C:18]([CH3:22])=[CH:17][C:16]=1[OH:23].CCCCCC.[C:30](OCC)(=[O:32])[CH3:31]>>[C:1]([O:23][C:16]1[CH:17]=[C:18]([CH3:22])[C:19]([NH:21][C:30](=[O:32])[CH3:31])=[CH:20][C:15]=1[CH3:14])(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8058HexaneHCID 8857Ethyl AcetateHCID 765444-Amino-2,5-dimethylphenol

Product 1

HCID 190786134-(Acetylamino)-2,5-dimethylphenyl acetateYield 95%

Procedure

Acetic anhydride (0.894 ml, 9.48 mmol) and pyridine (1 ml) were added to a solution of 2,5-dimethy-4-aminophenol (500 mg, 3.64 mmol) in ethyl acetate (5 ml), and the resulting mixture was refluxed. After 1 hour, hexane (50 ml) was poured into the reaction solution and the crystals formed were filtered under reduced pressure and then dried to obtain 4-(acetylamino)-2,5-dimethylphenyl acetate (763 mg, 95%).

Workup

  1. temperaturethe resulting mixture was refluxed
  2. customthe crystals formed
  3. filtrationwere filtered under reduced pressure
  4. customdried

Sources & evidence

ORD record
ord-47600a25813445e5981a0f8bc8a4c67a
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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