Hydrazine hydrate (1:1) → Bay-H-1127

HRID 502935Notes

Reaction equation

HRID 502935 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5].[NH2:14][NH2:15].O>CCCCO>[F:11][C:10]([F:12])([F:13])[C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[NH:15][N:14]=[C:4]2[NH2:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 5210162-Fluoro-5-(trifluoromethyl)benzonitrile

Product 1

HCID 16736Bay-H-1127

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2-Fluoro-5-trifluoromethyl-benzonitrile (2.66 g) was dissolved in n-BuOH (51 ml) prior to the addition of NH2NH2.H2O (1.02 ml). The solution was heated to reflux for 30 min. After cooling to rt, the solution was concentrated and CH2Cl2 was added. The organic layer was washed with H2O, brine, dried, filtered, and concentrated in high vacuum to give 5-trifluoromethyl-1H-indazol-3-ylamine (2.25 g): 1H NMR (DMSO, δppm, 300 mHz) 5.70 (s, br, 2H), 7.40 (dd, 2H), 8.20 (s, 1H), 11.90 (s, br, 1H).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 30 min
  3. concentrationthe solution was concentrated
  4. additionCH2Cl2 was added
  5. washThe organic layer was washed with H2O, brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated in high vacuum

Sources & evidence

ORD record
ord-958bd81a35f8429eb342cc6ebbb51120
Source dataset
uspto-grants-2010_08
Patent number
US07776884B2

Reaction notes

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