Hydrazine hydrate (1:1) → 4-iodo-1H-indazol-3-amine

HRID 2356361Notes

Reaction equation

HRID 2356361 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]>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

4

Reactant 2

HCID 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

Procedure

A mixture of 2-fluoro-6-iodobenzonitrile (5.040 g, 20 mmol), hydrazine hydrate (10 ml, 319 mmol) and n-butanol (100 mL) were heated at 110 C for 5 h and the mixture allowed to cool to rt. The mixture was partitioned between 100 mL EtOAc and 200 mL water and the layers separated. The aqueous layer was extracted with additional EtOAc (25 mL) and combined with organic layer. The combined organic layers were combined and washed with water, brine, dried over Na2SO4, filtered and evaporate. The title compound was obtained as an off-white solid (5.25 g). 1H NMR (400 MHz, dmso-d6) δ 11.79 (s, 1H), 7.34 (d, J=7.2 Hz, 1H), 7.27 (d, J=8.3 Hz, 1H), 6.90-6.95 (m, 1H), 5.04 (s, 2H).

Workup

  1. temperaturewere heated at 110 C for 5 h
  2. customThe mixture was partitioned between 100 mL EtOAc and 200 mL water
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with additional EtOAc (25 mL)
  5. washwashed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporate

Sources & evidence

ORD record
ord-9febdc19a6e54405bd5bfa2b2d083e67
Source dataset
uspto-grants-2010_07
Patent number
US07759344B2

Reaction notes

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