Methylhydrazine → 3-amino-1-methyl-1H-indazol-6-ol

HRID 1865206

Reaction equation

HRID 1865206 reaction equation
F[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[C:4]([OH:10])[CH:3]=1.[CH3:11][NH:12][NH2:13]>>[NH2:9][C:8]1[C:7]2[C:2](=[CH:3][C:4]([OH:10])=[CH:5][CH:6]=2)[N:12]([CH3:11])[N:13]=1

Participants

3

Reactant 2

HCID 6061MethylhydrazineHCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 1357424603-amino-1-methyl-1H-indazol-6-ol

Procedure

A solution of 6-fluoro-4-hydroxy benzonitrile (Aldrich, 10.1 g, 73.9 mmol) in methyl hydrazine (Aldrich, 20.0 mL, 379 mmol) was stirred at 80° C. for 16 h. After cooling to RT, the volatile portion was removed in vacuo. The residue was triturated with DCM and MeOH. The title compound was obtained by filtration as an off-white solid. The filtrate was concentrated in vacuo and purified by silica gel chromatography (DCM/MeOH: 100/0 to 95/5) to give an additional amount of the title compound as a white solid.

Workup

  1. customthe volatile portion was removed in vacuo
  2. customThe residue was triturated with DCM and MeOH

Sources & evidence

ORD record
ord-7ee42ce26a8c4b26a8c3756bbd828c1a
Source dataset
uspto-grants-2009_12
Patent number
US07626030B2

Linked notes

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