4-Ethylphenylhydrazine hydrochloride

150 ml of water and 160 ml of 12N hydrochloric acid are added to 24.2 g (0.2 mol) of 4-ethylaniline. The mixture is cooled to 0 C. and 14 g (0.2 mol) of sodium nitrite dissolved in 140 ml of water are then introduced dropwise. After 1 hour at 0 C., 112 g (0.496 mol) of stannous chloride dihydrate dissolved in 90 ml of 12 N hydrochloric acid are added to the reaction mixture, at 10 C. After 1 hour 30 at 10 C., the reaction mixture is ltered in order to obtain a brown solid, m.p.=198 C.; yield=95percent.General procedure: CuBr (36 mg, 0.25 mmol, 2.5 mol percent), L3 (110 mg, 0.4 mmol, 4 mol percent), H2O (0.5 mL), and K3PO4 (254 mg, 1.2 mmol) were mixedin a 15 mL screw cap test tube. After STAC (110 mg, 0.3 mmol, 3 mol percent) and aryl bromide (10 mmol) were added, the resulting mixture was stirred at 80-110° C (bath temperature) for 10 min.Then K3PO4 (2.29 g, 10.8 mmol) and N2H4*H2O (1 g, 20 mmol) were added and argon (flow rate 5-7 mL/min) was bubbled through thereaction mixture for 5 min.28 The reaction mixture was stirred ina closed test tube at 80-110° C (bath temperature) for 1-2 h until complete consumption of starting material was observed as monitoredby TLC (eluentehexane), then cooled to room temperatureand diluted with SH2Cl2 (50 mL). The resulting solutionwas filteredand washed with brine (225 mL). Aq HCl (37percent) was added to the CH2Cl2 solution dropwise until pH 3-4. The formed precipitate was filtered, washed with SH2Cl2 (15 mL) and dried atroom temperature. NMR spectra of certain synthesized aryl hydrazine hydrochlorides showed that they contained 1-5 mol percent of the corresponding aniline hydrochlorides as impurities (see Supplementary data). Analytical samples of aryl hydrazine hydrochlorides were purified via precipitation from methanol solution by adding 2-3 volumes of diethyl ether.

Molecular Weight:172.65
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:172.0767261
Monoisotopic Mass:172.0767261
Topological Polar Surface Area:38
Heavy Atom Count:11
Complexity:85.3
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes