Acetic Acid → HCID 2775180, compound

HRID 904674Notes

Reaction equation

HRID 904674 reaction equation
[NH2:1][C:2]1[C:3]([OH:13])=[C:4]([C:10](=[O:12])[CH3:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[C:14](O)(=[O:16])[CH3:15].C(OC(=O)C)(=O)C>O>[C:10]([C:4]1[C:3]([OH:13])=[C:2]([NH:1][C:14](=[O:16])[CH3:15])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 20478440HCID 20478440, compound

Product 1

HCID 2775180HCID 2775180, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

1-(3-Amino-2-hydroxy-6-methoxy-phenyl)ethanone (12.9 g) was added to a mixture of acetic acid (3 mls) and water (20 mls) and heated to 60° C. Acetic anhydride (9.5 mls) was then added and the whole heated on a steam bath for thirty minutes. The reaction mixture was poured into water and extracted into ether, which was dried using magnesium sulphate, and after filtration the volatiles were removed in vacuo, affording a golden brown solid which was triturated with chloroform and dried under reduced pressure, yielding 3.7 g of the sub title compound, mp 160°-162° C.

Workup

  1. temperaturethe whole heated on a steam bath for thirty minutes
  2. extractionextracted into ether, which
  3. customwas dried
  4. filtrationafter filtration the volatiles
  5. customwere removed in vacuo
  6. customaffording a golden brown solid which
  7. customwas triturated with chloroform
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-8b79a58404c34a03a2730deaf74bf21e
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

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