Methylhydrazine → 3-(2-hydroxyphenyl)-1-methyl-1H-pyrazole

HRID 1581778Notes

Reaction equation

HRID 1581778 reaction equation
[CH3:1][NH:2][NH2:3].O[CH:5]=[CH:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])=O>CO.O>[CH3:1][N:2]1[CH:5]=[CH:6][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[N:3]1

Participants

5

Reactant 2

HCID 6061MethylhydrazineHCID 26596986HCID 26596986, compound

Product 1

HCID 1355690293-(2-hydroxyphenyl)-1-methyl-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Methyl hydrazine (23.2 mmol, 1.23 ml) is added to a solution of 2-(3-hydroxy-2-propen-1-on-1yl)phenol (J. Am. Chem. Soc., 72:3396, 1950), 15.4 mmol, 2.54 g) in methanol (7 ml) and the mixture is heated at 100° C. for one hour. After cooling, the reaction mixture is diluted with water (100 ml) and stirred for one hour. The precipitate is collected via filtration and purified on silica gel (30% ethyl acetate/hexane) to give 811 mg of 2-(1-methylpyrazol-3-yl)phenol.

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate is collected via filtration
  3. custompurified on silica gel (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-dccf9d8a99ba41f893791f6989d67019
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Reaction notes

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