Ammonium Hydroxide → 1-(2-Amino-3-methylphenyl)ethan-1-one

HRID 1389394Notes

Reaction equation

HRID 1389394 reaction equation
C([NH:4][C:5]1[C:10]([C:11](=[O:13])[CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:14])(=O)C.[OH-].[NH4+]>O.C(O)C.Cl.S(=O)(=O)(O)O>[CH3:14][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([C:11](=[O:13])[CH3:12])[C:5]=1[NH2:4]

Participants

7

Reactant 2

HCID 14923Ammonium HydroxideHCID 15581073HCID 15581073, compound

Product 1

HCID 1796281-(2-Amino-3-methylphenyl)ethan-1-oneYield 83%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

N-Acetyl-2-methyl-6-acetylaniline (76.1 g) in water (300 ml), ethanol (300 ml), concentrated hydrochloric acid (300 ml) and concentrated sulfuric acid (15 ml) were refluxed for 24 hours. The solution was cooled and concentrated ammonium hydroxide was added to pH 10. The solution was extracted with dichloromethane. The extracts were dried (MgSO4) and stripped. 2-methyl-6-acetylaniline (49.3 g) was obtained as a tan solid.

Workup

  1. temperatureThe solution was cooled
  2. extractionThe solution was extracted with dichloromethane
  3. dry with materialThe extracts were dried (MgSO4)

Sources & evidence

ORD record
ord-4f220d9e848842fc9a407f508b5f4e63
Source dataset
uspto-grants-1981_01
Patent number
US04244730

Reaction notes

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