Dimethyl Sulfate → 3-Methoxy-2-methylaniline

Participants

Reaction Conditions

Reaction Steps

2.24 g (20 mmol, 2 eq) of potassium tert-butoxide is dissolved in 60 ml of anhydrous THF and the resulting solution is cooled to −15° C. with stirring. A solution of 2.51 g (10 mmol, 1 eq) of 3-amino-6-iodo-2-methyl-2-cyclohexen-1-one in 25 ml anhydrous THF is added to the potassium tert-butoxide solution and the temperature is kept below −5° C. during addition. The cooling bath is removed after addition and the reaction is allowed to warm up to 5° C. within 1 hour. HPLC shows complete elimination. 1.20 g (9.5 mmol, 0.95 eq) of dimethyl sulfate is added to the reaction mixture with vigorous Stirring. The reaction is shown to be complete by HPLC (˜2 h). Then an HPLC weight assay indicates an 89% yield of the product. The isolation of the product was not optimized.

Provenance & Evidence