Water → HCID 19775932, compound

Participants

Reaction Steps

The nitroaniline obtained in step A (2 g, 6.6 mmol) was dissolved in 50% aqueous ethanol (100 cm3) and sodium dithionite (4.61 g 26.5 mmol) added portionwise over 20 minutes to the stirred solution, each portion being allowed to dissolve before adding the next. The reaction mixture was heated under reflux with stirring for 1.5 hours and after cooling was poured into water (50 cm3) and neutralised with aqueous sodium bicarbonate before being extracted with ethyl acetate (2×100 cm3). The combined extracts were dried (MgSO4) and the solvent removed in vacuo leaving a light brown solid which was triturated with hexane, filtered and dried, to give 4-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yloxy)-o-phenylenediamine m.p. 109°-111° C.

Provenance & Evidence