Stannous chloride dihydrate → (1H-Indazol-5-yl)-hydrazine hydrochloride

HRID 1930324Notes

Reaction equation

HRID 1930324 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH2:10])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[N:11]([O-])=O.[Na+].O.O.[Cl:17][Sn]Cl>Cl>[ClH:17].[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][NH2:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 880121H-Indazol-5-amineHCID 23668193Sodium Nitrite

Product 1

HCID 67271720(1H-Indazol-5-yl)-hydrazine hydrochloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

To a solution of 1H-indazol-5-ylamine (20 g, 153 mmol) in cone. HCl (50 mL) was added an aqueous solution (50 mL) of NaNO2 (19 g, 158 mmol) at 0° C. and the resulting mixture was stirred for 1 h. A solution of SnCl2.2H2O (90 g, 306 mmol) in cone. HCl (70 mL), pre-cooled to 0° C., was then added. The reaction solution was stirred for 2 h at RT. The precipitate was filtered and washed with ether to yield (1H-indazol-5-yl)-hydrazine hydrochloride as a yellow solid, which was used for the next reaction without further purification.

Workup

  1. additionwas then added
  2. stirringThe reaction solution was stirred for 2 h at RT
  3. filtrationThe precipitate was filtered
  4. washwashed with ether

Sources & evidence

ORD record
ord-d87f8cd3079e4a22bad8cf9cffea2ae2
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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