Water → 4-iodo-1H-indazol-3-amine

HRID 1430363Notes

Reaction equation

HRID 1430363 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[C:4]#[N:5].O.[NH2:12][NH2:13].O>C(O)CCC>[I:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]2[C:3]=1[C:4]([NH2:5])=[N:12][NH:13]2

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 5227222-Fluoro-6-iodobenzonitrile

Product 1

HCID 40577874-iodo-1H-indazol-3-amine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
107.5 °C

Procedure

A mixture of 2-fluoro-6-iodobenzonitrile (2 g, 8.1 mmol) and hydrazine hydrate (4 mL) in n-butanol (40 mL) was heated to 105-110° C. for 5 hours, cooled to room temperature, poured into water, and extracted twice with ethyl acetate. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated to provide 1.88 g of the desired product. Rf=0.25 (5% methanol/dichloromethane).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted twice with ethyl acetate
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-30a9287811ce44a5b4dd9e5b671f193f
Source dataset
uspto-grants-2015_01
Patent number
US08940778B2

Reaction notes

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