Sulfuric Acid → Methyl 3-amino-2,4,6-trimethylphenylacetate

HRID 2229903Notes

Reaction equation

HRID 2229903 reaction equation
[C:1]([CH2:3][C:4]1[C:5]([CH3:13])=[C:6]([C:8]([CH3:12])=[CH:9][C:10]=1[CH3:11])[NH2:7])#N.S(=O)(=O)(O)[OH:15].[C:19](=O)([O-])[O-:20].[Na+].[Na+]>CO.O>[NH2:7][C:6]1[C:5]([CH3:13])=[C:4]([CH2:3][C:1]([O:20][CH3:19])=[O:15])[C:10]([CH3:11])=[CH:9][C:8]=1[CH3:12]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 108449753-Cyanomethyl-2,4,6-trimethylaniline

Product 1

HCID 10560264Methyl 3-amino-2,4,6-trimethylphenylacetateYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 3-cyanomethyl-2,4,6-trimethylaniline (see Example 14, procedure C) (5 g, 28.7 mmol) in methanol (30 mL) was added concentrated sulfuric acid (30 mL) with cooling. The resulting mixture was heated under reflux for 8 h before it was allowed to cool to rt and diluted with water (100 mL). The mixture was stripped off methanol and the residue was basified with sodium carbonate and then extracted with ethyl acetate. The organic layer was worked up and concentrated as usual to give the desired compound as an oil (5.2 g, 88%).

Workup

  1. temperaturewith cooling
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 8 h before it
  4. extractionextracted with ethyl acetate
  5. concentrationconcentrated as usual

Sources & evidence

ORD record
ord-b47951e02e7e46fc8bafa2f30a51b8a4
Source dataset
uspto-grants-2002_07
Patent number
US06420567B1

Reaction notes

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