3-Fluorophenylhydrazine hydrochloride

white to light yellow crystal powde

4) salt [0026] A mixture of 22. lg 3-fluorophenylhydrazine was dissolved in 15.4 ml of 37percent hydrochloric acid and stirred at 65 ° C until the reaction solution was precipitated Crystallization, cooling to 20 ° C, filtration, with acetone leaching filter cake, after drying to be 3-fluorophenylhydrazine hydrochloride products 24. 4g, content 99. 2percent yield of 39. 1percentTo a solution of (3-fluorophenyl)hydrazine HCI-salt (25 g, 153.7 mmol) and tert-butyl 3- oxopiperidine-1 -carboxylate (30.59 g, 153.7 mmol) in 1 , 4-dioxane (250 mL) was added cone. H2SO4(25 mL), 0 C. Then the reaction mixture was heated at 1 10 C for 3 h. The reaction mixture was cooled to 25 C and the precipitate was filtered off. The solid was dissolved in water basified with NaOH solution and extracted with dichloromethane. The organic phase was separated, dried over Na2S04, filtered and the solvent was removed under reduced pressure to afford the cyclized title compounds as a pale brown solid (23 g). The crude mixture of regioisomers was taken as such for next step.MS: 191 (M+H)+. Step BTo a solution of the title compound from Step A above (23 g, 121.05 mmol) in THF (250 mL) was added triethylamine (33.7 mL, 242.1 mmol ) and di-ferf-butyl dicarbonate (32 g, 145.2 mmol) and the reaction mixture was stirred for 12 h. After the completion of the reaction as evidenced by TLC, the solvent was removed under reduced pressure and the crude reaction mixture was purified by flash column chromatography using hexane/ ethyl acetate (80:20) to afford the title compounds as a pale yellow solids (7 g, 20%). MS: 191.2 (M-Boc)+.in room temperature, N-methylquinoxaline-2 (1H) -one (0.1 mmol) was sequentially added to a 5 mL photoreaction tube.3-fluoromethylphenylhydrazine hydrochloride (0.3 mmol), 2D-COF-1 (4 mg), K2CO3 (0.3 mmol) and dimethyl sulfoxide (1.5 mL). Stir in the air for 24 hours under the irradiation of a blue LED lamp with a power of 34W and a wavelength of 400-500nm. The reaction was stopped, extracted with ethyl acetate and water, and then concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and the corresponding quinoxalinone derivative was obtained by flash column chromatography (silica gel column) (light yellow solid 19 mg, yield 75%).General procedure: A mixture of alkynone 1 or 2 (1 equiv), arylhydrazine 8-14(1.2 equiv), and Et3N (5 equiv) in anhydrous EtOH (50 ml)was refluxed for 9 h. The reaction mixture was evaporated, the residue was purified by silica gel column chromatography(eluent CHCl3).

Molecular Weight:162.59
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:162.0360041
Monoisotopic Mass:162.0360041
Topological Polar Surface Area:38
Heavy Atom Count:10
Complexity:87.1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes