3,4-Dichloroaniline → HCID 178526503, compound

Participants

Reaction Steps

A solution of 2-chloro-8-(1,3-dioxolan-2-yl)-4-hydroxy-6-nitroquinazoline (2.9 g), 3,4-dichloroaniline (3.2 g) and N,N-diisopropylethylamine (2.52 mL) in N,N-dimethylacetamide (145 mL) was heated to 140° C. for 3.3 hours. The mixture was then cooled to room temperature and diluted with water (2 L). The aqueous solution was separated into two equal portions, and each portion was extracted with ethyl acetate (7×100 mL). The combined ethyl acetate extracts were washed with 2N hydrochloric acid until all of the excess 3,4-dichloroaniline was removed, dried over Na2SO4, filtered and evaporated to afford the title compound as a brown solid (2.6 g). 1H NMR (300 MHz, DMSO-d6): 8.67 (d, J=2.7 Hz, 1H), 8.48 (d, J=2.7 Hz, 1H), 8.45 (d, J=2.7 Hz, 1H), 7.58 (d, J=8.7 Hz, 1H), 7.42 (dd, J=2.7, 8.7 Hz, 1H), 6.23 (s, 1H), 4.09 (m, 4H). HPLC Method A: 7.76 min.

Provenance & Evidence