Pyridine → HCID 22142146, compound

Reaction equation

Cl.[F:2][C:3]([F:20])([F:19])[C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[O:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][NH2:15])=[CH:10][CH:9]=1.N1C=CC=CC=1.Cl[C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29]>C(OCC)(=O)C>[F:2][C:3]([F:19])([F:20])[C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[O:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][NH:15][C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29])=[CH:12][CH:13]=1

Participants

Procedure

To a suspension of 4-[3-(trifluoromethyl)phenoxy]phenylhydrazine hydrochloride (11 g) and pyridine (6.0 mL) in ethyl acetate (100 mL) at 0° C. was added dropwise isopropyl chloroformate (38 mL, 1M in toluene) over a period of 30 min. The mixture was then stirred at room temperature for 5 hour, quenched with 1M aqueous HCl (100 mL). The organic layer was separated, washed twice with water (100 mL), dried over anhydrous sodium sulfate, and finally evaporated under reduced pressure to yield a light brown solid (11 g).