Dimethyl Sulfate → 3-Methoxy-2-methylaniline
Reaction equation
[CH3:1]C(C)([O-])C.[K+].[NH2:7][C:8]1[CH2:13][CH2:12][CH:11](I)[C:10](=[O:15])[C:9]=1[CH3:16].S(OC)(OC)(=O)=O>C1COCC1>[CH3:1][O:15][C:10]1[C:9]([CH3:16])=[C:8]([CH:13]=[CH:12][CH:11]=1)[NH2:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -15 °C
Procedure
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.
Workup
- additionthe temperature is kept below −5° C. during addition
- customThe cooling bath is removed
- additionafter addition
- temperatureto warm up to 5° C. within 1 hour
- customto be complete by HPLC (˜2 h)
Sources & evidence
- ORD record
- ord-c6492f5d676644e28586aaa21ead6f23
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07642381B2
Reaction notes
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