Ammonium Chloride → 3-Acetoxymethyl-2,4,6-trimethylaniline

HRID 2229916Notes

Reaction equation

HRID 2229916 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[C:8]([N+:14]([O-])=O)[C:7]=1[CH3:17])(=[O:3])[CH3:2].[Cl-].[NH4+]>CO.[Zn]>[C:1]([O:4][CH2:5][C:6]1[C:7]([CH3:17])=[C:8]([C:9]([CH3:13])=[CH:10][C:11]=1[CH3:12])[NH2:14])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 152542861-Acetoxymethyl-3-nitro-2,4,6-trimethylbenzene

Product 1

HCID 106559423-Acetoxymethyl-2,4,6-trimethylanilineYield 75%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-acetoxymethyl-3-nitro-2,4,6-trimethybenzene (6.0 g, 25.2 mmol) in methanol (100 mL) were sequentially added ammonium chloride (2.7 g in 25 mL of water), zinc powder (11 g). The exothermic reaction was vigorously stirred until it was back to RT (2 h). To work up the crude mixture was filtered off and the cake was washed with methanol. The methanolic solutions were concentrated to a volume of 20 mL, added 1N HCl (300 mL). The insoluble material was removed by filtration, the solution was basified with solid NaHCO3. The semicrystalline precipitate was taken into ethyl acetate. The extract was concentrated and the residual product purified by means of column chromatography (25% ethyl acetate/hexane) to give 3-Acetoxymethyl-2,4,6-trimethylaniline as a pink oil (3.8 g, 75%).

Workup

  1. customThe exothermic reaction
  2. customwas back to RT
  3. custom(2 h)
  4. filtrationwas filtered off
  5. washthe cake was washed with methanol
  6. concentrationThe methanolic solutions were concentrated to a volume of 20 mL
  7. additionadded 1N HCl (300 mL)
  8. customThe insoluble material was removed by filtration
  9. concentrationThe extract was concentrated
  10. customthe residual product purified by means of column chromatography (25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ef270720e8be4dbd97dee951302bf1e4
Source dataset
uspto-grants-2002_07
Patent number
US06420567B1

Reaction notes

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