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2-AMINO-4,6-DIMETHYL-BENZOIC ACID METHYL ESTER synthesis

4synthesis methods
2H-3,1-Benzoxazine-2,4(1H)-dione, 5,7-dimethyl-

147494-08-4
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2-AMINO-4,6-DIMETHYL-BENZOIC ACID METHYL ESTER

35490-78-9
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Yield:35490-78-9 86%

Reaction Conditions:

with sodium hydroxide in methanol;ethyl acetate;

Steps:

7.d d.

d. Methyl 2-amino-4,6-dimethylbenzoate 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).

References:

US5599814,1997,A