Water → 4-iodo-1H-indazol-3-amine

HRID 497602Notes

Reaction equation

HRID 497602 reaction equation
O.[NH2:2][NH2:3].F[C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([I:13])[C:6]=1[C:7]#[N:8].O>C(O)C>[I:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:5]2[C:6]=1[C:7]([NH2:8])=[N:2][NH:3]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 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

1.2 cm3 of hydrazine monohydrate are added to 2 g of 2-fluoro-6-iodobenzonitrile in 25 cm3 of ethanol. The reaction medium is then refluxed at about 78° C. for 12 hours. The medium is allowed to return to about 20° C. and 20 cm 3 of distilled water are then added in order to precipitate the product. The insoluble material is filtered on a sinter funnel, rinsed with 20 cm3 of distilled water and then taken up in 20 cm3 of dichloromethane. The organic phase is then dried over magnesium sulphate and evaporated under reduced pressure (2 kPa; 45° C.). After drying (90 Pa; 50° C.), 1.65 g of 4-iodo-1H-indazole-3-amine are obtained in the form of a yellow solid melting at 157° C.

Workup

  1. customto return to about 20° C.
  2. customto precipitate the product
  3. filtrationThe insoluble material is filtered on a sinter funnel
  4. washrinsed with 20 cm3 of distilled water
  5. dry with materialThe organic phase is then dried over magnesium sulphate
  6. customevaporated under reduced pressure (2 kPa; 45° C.)
  7. dry with materialAfter drying (90 Pa; 50° C.), 1.65 g of 4-iodo-1H-indazole-3-amine

Sources & evidence

ORD record
ord-2ae53273fb014e0881c0daf7302f8d3a
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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