5-Chloro-2-methylaniline → HCID 18324843, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-chloro-2-methylaniline (10.1 g) and 3-bromo-1-propanol (2.5 mL) were heated at 100° C. under nitrogen for 45 minutes. After cooling, a solid mass formed which was partitioned between dichloromethane and 1N sodium hydroxide. The organic phase 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 20% ethyl acetate in hexane gave the title compound (5.6 g, 98.1%) as a brown oil, which was used as such in the next step.

Provenance & Evidence