Hydrazine hydrate (1:1) → HCID 617104, compound
Reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[C:5]([N:26]3C(=O)C4=CC=CC=C4C3=O)[CH:6]=[C:7]([O:24][CH3:25])[C:8]=2[O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[N:3]=1.O.NN>C(O)C>[NH2:26][C:5]1[CH:6]=[C:7]([O:24][CH3:25])[C:8]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=2)=[C:9]2[C:4]=1[N:3]=[C:2]([Cl:1])[CH:11]=[C:10]2[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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.