Hydrazine hydrate (1:1) → HCID 617104, compound

Participants

Reaction Steps

A suspension of 2-chloro-6-methoxy-4-methyl-8-phthalimido-5-(3-trifluoromethylphenoxy)quinoline (23.2 g, 45.2 mmol) in ethanol (900 mL) was treated with excess hydrazine hydrate (75%, 16.75 mL) and the mixture was refluxed with mechanical stirring for 3 hours. After cooling, the solids were collected and washed with CH2Cl2. The combined filtrate and washings were evaporated in vacuo to a small volume and dissolved in CH2Cl2 ( 500 mL). The solution was extracted with 20% KOH (3×200 mL), and with brine, dried (K2CO3) and evaporated in vacuo to an amber gum. Recrystallization from cyclohexane-ligroin (5:2, 500 mL) with charcoaling gave 15.4 g (89%) of 1st crop title compound, mp 133°-135° C. Further recrystallization did not change the melting point.

Provenance & Evidence