Benzenamine, 3-bromo-4-methyl- → HCID 86687579, compound

Participants

Reaction Conditions

Reaction Steps

To a vial charged with 3-bromo-4-methylaniline (1.00 g, 5.37 mmol) was added IPA (10.75 ml) and 5-(methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1.001 g, 5.37 mmol) respectively. The mixture was heated to 90° C. for 2 hrs, providing a brown solution which was cooled to room temperature, yielding an orange precipitate which was collected by vacuum filtration affording 5-(((3-bromo-4-methylphenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1.535 g, 4.51 mmol, 84% yield). This solid was transferred to a 5-20 ml microwave vial and 9 ml (0.5M 1,2-dichlorobenzene) was added and the mixture irradiated at 225° C. for 15 min, affording conversion to desired product according to LC-MS. To the suspension was added diethyl ether (˜5 ml) to aid in product precipitation. The precipitate was collected via vacuum filtration and washed with ether, affording a brown solid as an isomeric mixture (560 mg). To the filtrate which had some precipitate forming was added heptane affording additional precipitate. This second crop was collected affording another 115 mg of product (53% yield total). m/z (ESI) 238.1/240.1 (M+H)+.

Provenance & Evidence