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ChemicalBook CAS DataBase List 3-Methoxy-2-methylaniline
19500-02-8

3-Methoxy-2-methylaniline synthesis

5synthesis methods
-

Yield: 89%

Reaction Conditions:

Stage #1:3-amino-6-iodo-2-methyl-2-cyclohexen-1-one with potassium tert-butylate in tetrahydrofuran at -15 - 5; for 1 h;
Stage #2:dimethyl sulfate in tetrahydrofuran at 5; for 2 h;

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 0C with stirring. A solution of 2.51 g (10 mmol, 1 eq) of 3-amino-6-iodo-2-methyl-2-cyclohexen-l-one in 25 ml anhydrous THF is added to the potassium tert-butoxide solution and the temperature is kept below -5 0C during addition. The cooling bath is removed after addition and the reaction is allowed to warm up to 5 0C within lhour. HPLC shows complete elimination. 1.20 g (9.5 romol, 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.

References:

BOEHRINGER INGELHEIM INTERNATIONAL GMBH;BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG WO2007/130704, 2007, A1 Location in patent:Page/Page column 6-7

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