Hydrazine hydrate (1:1) → 7-(Trifluoromethyl)-1H-indazole

HRID 1817486Notes

Reaction equation

HRID 1817486 reaction equation
F[C:2]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.O.[NH2:15][NH2:16]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[F:11][C:10]([F:13])([F:12])[C:9]1[CH:8]=[CH:7][CH:6]=[C:3]2[C:2]=1[NH:16][N:15]=[CH:4]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 5179782-Fluoro-3-(trifluoromethyl)benzaldehyde

Product 1

HCID 203239087-(Trifluoromethyl)-1H-indazoleYield 93%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 2-fluoro-3-trifluoromethylbenzaldehyde (5 g, 26 mmol)), hydrazine hydrate (8.3 mL, 260 mmol) and DMAP (3.17 g, 26 mmol.) in 10 mL pyridine was heated at 100° C. for 24 hours. The cool reaction mixture was partitioned with EtOAc and 1 N HCl. The organic phase was washed with brine and dried with anhydrous sodium sulfate (Na2SO4). The organic phase was concentrated in vacuo to give 4.5 g of product. The crude product was recrystallized from Et2O/hexane to give the title compound (3.6 g, white solid, mp 90° C.).

Workup

  1. customThe cool reaction mixture
  2. customwas partitioned with EtOAc and 1 N HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried with anhydrous sodium sulfate (Na2SO4)
  5. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-f978f2f0528545849537cc26efce81cb
Source dataset
uspto-grants-2009_10
Patent number
US07598286B2

Reaction notes

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