3-Bromo-o-toluidine → HCID 86687589, compound

Participants

Reaction Conditions

Reaction Steps

To a vial charged with 3-bromo-2-methylaniline (1.207 g, 6.49 mmol) was added IPA (12.98 ml) and 5-(methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1.208 g, 6.49 mmol) respectively. The mixture was heated to 90° C. for 2 hr providing a brown solution which was cooled to room temp affording an orange precipitate which was collected by vacuum filtration affording 5-(((3-bromo-2-methylphenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1.71 g, 5.03 mmol, 77% yield). This solid was transferred to a 5-20 ml microwave vial and 10 ml (0.5M 1,2-dichlorobenzene) was added and the mixture irradiated at 225° C. for 15 mins affording conversion to desired product according to LC-MS. Much precipitate was present directly following irradiation and cooling. The solid was collected via vacuum filtration and washed with heptane and dried under reduced pressure affording product as a brown solid 7-bromo-8-methylquinolin-4-ol (1.008 g, 4.23 mmol, 65.3% yield). m/z (ESI) 238.1 (M+H)+.

Provenance & Evidence