Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)

white to pink crystalline powder

The reaction vessel was charged with reaction materials: 98.25 g of p-bromochlorobenzene and 3.3 equivalents of hydrazine hydrate, hydrazine hydrateThe degree is 71percent, adding 10percent by weight of a phase transfer catalyst (PEG400), 3 times by weight of a solvent (propylene glycol), and 20percent by weight of a catalyst (3:1 mass ratio of copper sulfate and cobalt chloride). The reaction; the reaction process includes: slowly warming and control the temperature to 152 ° C, normal pressure reflux or packing pressure reaction, maintaining the temperature reaction 10h, sampling HPLC detection of p-chlorophenylhydrazone no longer increase, that is, stop the reaction.After the reaction was completed, the solid was separated by filtration and the filtrate was distilled to remove the solvent.To the residue obtained in Step B was added 30percent hydrochloric acid, the pH was adjusted to 3, and the mixture was thoroughly stirred and filtered.The filter residue was washed with water and dried at 55°C to obtain p-chlorophenylhydrazine hydrochloride. In this example, the yield of p-chlorophenylhydrazine hydrochloride was 88.1percent, and the HPLC content was 99.29percent.in an equivalent ratio of 1: 2.8 for p-bromochlorobenzene, hydrazine hydrate as the reaction raw material, The reaction was carried out by adding a phase transfer catalyst (benzo-18-crown-6), a solvent (90percent aqueous solution of propylene glycol) and a catalyst (cuprous bromide), wherein the concentration of hydrazine hydrate was 59.5percent phase transfer catalyst, The weight ratio of the catalyst is 1: 0.15: 0.2, the weight ratio of bromochlorobenzene to the solvent is 1: 16.6; The reaction process involves slowly raising the temperature and controlling the temperature to 172 °C, Holding pressure reaction, keep the temperature reaction 5h, Sampling HPLC was detected until p-chlorophenylhydrazine was no longer increased, ie, the reaction was stopped. After completion of the reaction, the solid was separated by filtration and the filtrate was distilled off to remove the solvent. To the residue obtained in step B was added 24.8percent hydrochloric acid, adjusted to pH 1.8, And then fully stirred and filtered. the filter residue washed, 70 °C to obtain p-chlorophenylhydrazine hydrochloride. In this example, the yield of p-chlorophenylhydrazine hydrochloride was 86.3percent and the HPLC content was 99.2percent.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.A solution of 4-chloroaniline (127.6 g, 1 mol) in concentrated hydrochloric acid (293 mL) was stirred for 2 h at room temperature. To a solution of sodium nitrite (72.5 g, 1.05 mol) in water (145 mL) was added dropwise below 5 °C. After stirring 1 h, filtrate was separated by filtration, to which a solution of NaHSOUsing a tubular reactor with an inner diameter of 32 mm, A 20 g (20-40 mesh) Pd / C103 catalyst was charged, Chlorinated diazo-chlorobenzene is dissolved in water, To obtain a solution for catalysis, Hydrogenation reduction experiment,

Used as an intermediate in organic synthesis; used in dyes and pharmaceutical intermediates.

Molecular Weight:179.04
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:178.0064537
Monoisotopic Mass:178.0064537
Topological Polar Surface Area:38
Heavy Atom Count:10
Complexity:79.1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes