Hydrazine → HCID 76846136, compound

HRID 246034Notes

Reaction equation

HRID 246034 reaction equation
F[C:2]1[C:9]([F:10])=[C:8]([F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:12][NH2:13]>O1CCOCC1>[F:11][C:8]1[C:9]([F:10])=[C:2]2[C:3]([CH:4]=[N:12][NH:13]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 5192262,3,4-Trifluorobenzaldehyde

Product 1

HCID 76846136HCID 76846136, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

In a microwave vial 2,3,4-trifluorobenzaldehyde (1.5 g, 9.4 mmol) was dissolved in 1,4-dioxane (6 mL) and hydrazine (6 mL, 191 mmol) was added. The vial was sealed and heated under microwave irradiation at 150° C. for 30 min. The reaction was quenched with water and extracted with EtOAc. The organic layer was washed with brine then dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography with 20% to 50% EtOAc/heptane to provide 664 mg (46%) of 6,7-difluoro-1H-indazole as a light brown powder. 1H NMR (CDCl3, 300 MHz): δ (ppm) 8.10 (d, J=3.4 Hz, 1H), 7.47 (dd, J=8.9, 4.0 Hz, 1H), 7.05 (ddd, J=10.6, 8.9, 6.6 Hz, 1H).

Workup

  1. customThe vial was sealed
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialthen dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography with 20% to 50% EtOAc/heptane

Sources & evidence

ORD record
ord-80b0c9ebcc3e4c72aea0aa352bb56dfe
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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