Sodium Hydroxide → Methyl 2-amino-4,6-dimethylbenzoate

HRID 3110Notes

Reaction equation

HRID 3110 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[C:9]2[C:10](=[O:15])[O:11][C:12](=O)[NH:13][C:8]=2[CH:7]=[C:6]([CH3:16])[CH:5]=1>CO>[NH2:13][C:8]1[CH:7]=[C:6]([CH3:16])[CH:5]=[C:4]([CH3:3])[C:9]=1[C:10]([O:11][CH3:12])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 189298545,7-Dimethyl-2H-3,1-benzoxazine-2,4(1H)-dione

Product 1

HCID 18929833Methyl 2-amino-4,6-dimethylbenzoateYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of sodium hydroxide (0.013 g, 0.33 mM) in methanol (1.7 mL) was added 5,7-dimethyl-2H-3,1-benzoxazine-2,4(1H)-dione (0.67 g, 3.5 mM). The mixture was heated to 60° C. and maintained at that temperature for 45 min during which vigorous gas evolution ensued and all solids dissolved completely. The solution was cooled and concentrated using a rotary evaporator. The residue was dissolved in ethyl acetate, and the ethyl acetate solution was washed with water, dried (Na2 SO4), filtered and concentrated to provide the title compound (0.54 g, 86%) as a tan solid; MS(CI); 180 (M+H).

Workup

  1. temperaturemaintained at that temperature for 45 min during which vigorous gas evolution
  2. dissolutionall solids dissolved completely
  3. temperatureThe solution was cooled
  4. concentrationconcentrated
  5. customa rotary evaporator
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washthe ethyl acetate solution was washed with water
  8. customdried (Na2 SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-1a81f6348ff444b79db47e60e3184959
Source dataset
uspto-grants-1998_03
Patent number
US05733910

Reaction notes

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