5-Amino-3-methyl-1-phenylpyrazole

Yellow crystalline powder

General procedure: In a 2-5mL microwave vial containing a stir bar, 3-aminocrotonitrile (164 mg, 2mmol) and 5 mL of 1M HCl were combined with stirring to give a 0.4 M solution of starting material. Next, phenylhydrazine (216 mg, 2 mmol) was added to the solution. The microwave vial was then sealed with an aluminum cap and irradiated in the microwave reactor at 150 °C for 10 m with the absorbance set to “very high.” After cooling, the orange sludge-containing heterogeneous solution was basified with 10percent NaOH and was sonicated for 5 m to produce a visible solid precipitate. The precipitate was filtered, washed twice with D.I. water, and then dried to yield the product as a light orange solid (292 mg, 84percent yield). For compounds that do not readily precipitate, the product can be isolated by extracting the basic aqueous layer 3x with dichloromethane (DCM). The combined organic layers are dried over magnesium sulfate, filtered and evaporated under reduced pressure to obtain the product.Step-1: To a stirred solution of 3-aminocrotononitrile (60 gm, ) and 1N HCl (600 ml) was added phenyl hydrazine (72 ml). The reaction mass was strirred for 4 firs at 110-115° C. The reaction mixture was cooled to 25-30° C. and quenched in ice water (3.0 lit). This was then neutralised with sodium bicarbonate solution. The precipitated solid was then stirred, filtered and dried to get 110 gm of the title compound. (0201) On the β-iminobutironitrile formed there were added 36 mL (0, 36 mol) of phenylhydrazine and 50ml of a 2:1 solution (v/v) of chloride acid and water. The mixture remained under magnetic agitation and heating at the reflux temperature for 30 minutes. The ending of the reaction was indicated by c.c.f. (mixture 1 :1 v/v of ethyl acetate and petroleum ether as eluant). The reaction mixture, then, was poured on frozen water and the environment was neutralized with NaOH 10percent solution, being obtained a orange precipitate at 90percent of yield. This, after clearing in ethanol and water until turbidity, supplied PF= 1100C.RMN - To a solution of (Z)-3-aminobut-2- enenitrile (4 g, 48.78 mmol) in MeOH (20 mL), HC1 (10 mL) at 0 °C and phenylhydrazine (3.1 g, 29.26 mmol) was added and heated at 90 °C for 2 h. Progress of the reaction was monitored by TLC. Upon completion the reaction mixture was evaporated under reduced pressure to obtain a residue. The crude product was purified by column chromatography to afford 3 -methyl- 1 -phenyl- lH-pyrazol-5- amine (1 g, 15.62percent) and 5-methyl-l-phenyl-lH-pyrazol-3-amine (0.9 g, 14.06percent)

Used as intermediate for dyes and medicine

Molecular Weight:173.21
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:173.095297364
Monoisotopic Mass:173.095297364
Topological Polar Surface Area:43.8
Heavy Atom Count:13
Complexity:166
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes