Hydrochloric Acid → 1-(5-Amino-2-methoxyphenyl)ethanone

HRID 1870231Notes

Reaction equation

HRID 1870231 reaction equation
Cl.[C:2]([C:5]1[CH:6]=[C:7]([NH:13]C(=O)C)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])(=[O:4])[CH3:3]>C(O)C>[NH2:13][C:7]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:5]([C:2](=[O:4])[CH3:3])[CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 28174183-Acetyl-4-methoxyacetanilide

Product 1

HCID 155794431-(5-Amino-2-methoxyphenyl)ethanoneYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrochloric acid (6M, 50 ml) was added to a mixture of N-(3-acetyl-4-methoxyphenyl)acetamide (10.34 g, 50 mmol) and ethanol (150 ml) and the mixture was stirred under reflux for 8 hours. The mixture was cooled and the solvent was evaporated under reduced pressure. Water (100 ml) was added and the pH was adjusted to 10.0 with saturated aqueous potassium carbonate. The mixture was extracted with dichloromethane (3×100 ml) and the combined organic fractions were dried (MgSO4) and evaporated under reduced pressure to give 1-(5-amino-2-methoxyphenyl)ethanone as a dark oil (8.16 g, 99%), 1H NMR (CDCl3) δ 7.09 (1H, d, J=2.8 Hz), 6.82 (2H, m), 3.84 (3H, s), and 3.34 (2H, br. s), 2.59 (3H, s). m/e (CI+) 166 (MH+).

Workup

  1. temperatureunder reflux for 8 hours
  2. temperatureThe mixture was cooled
  3. customthe solvent was evaporated under reduced pressure
  4. additionWater (100 ml) was added
  5. extractionThe mixture was extracted with dichloromethane (3×100 ml)
  6. dry with materialthe combined organic fractions were dried (MgSO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-39087a7182c54c0ba1cf02090bca77d2
Source dataset
uspto-grants-2000_08
Patent number
US06096766

Reaction notes

Loading…