Hydrochloric Acid → n-(5-methoxy-2-methylphenyl)acetamide

HRID 1773588Notes

Reaction equation

HRID 1773588 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:17])=[C:14]([NH2:16])[CH:15]=1.O.Cl>N1C=CC=CC=1>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:17])=[C:14]([NH:16][C:1](=[O:3])[CH3:2])[CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 995005-Methoxy-o-toluidine

Product 1

HCID 231720n-(5-methoxy-2-methylphenyl)acetamideYield 90.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (5.6 g, 54.66 mmol) was added to a solution of 5-methoxy-2-methyl-phenylamine (5.0 g, 36.44 mmol) in pyridine (30 mL) and the resulting mixture was stirred at room temperature overnight. Water was added and the pH was adjusted to 5 by addition of an aqueous solution of hydrochloric acid (3 M). The resulting mixture was extracted with dichloromethane; the organic layer was separated and washed with a saturated aqueous solution of sodium bicarbonate and with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford 5.93 g of N-(5-methoxy-2-methyl-phenyl)-acetamide as a white solid without further purifications.

Workup

  1. extractionThe resulting mixture was extracted with dichloromethane
  2. customthe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium bicarbonate and with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8bf8c2f704f24db19d00340d347e8847
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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