4-Chloro-2-toluidine → HCID 18324828, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-2-methylaniline (35.7 g) and 3-bromo-1-propanol (8.75 g) was heated at 100° C. under nitrogen for 1 hour. After cooling, a solid mass formed which was partitioned between dichloromethane and 1N sodium hydroxide. The organic layer was washed with brine, dried over anhydrous potassium carbonate and concentrated in vacuo to give a brown oil. The crude material was dissolved in dichloromethane and absorbed onto a column of Merck-60 flash silica gel. Elution with a solvent gradient (from 100% dichloromethane to 95:5 dichloromethane-methanol) provided the title product (18.0 g, 90%) as a brown oil, which was used as such in the next step.

Provenance & Evidence