6-Aminoquinoline → 6-Hydrazinylquinoline hydrochloride

HRID 599306Notes

Reaction equation

HRID 599306 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[N:12]([O-])=O.[Na+].O.O.[Cl:18][Sn]Cl>Cl>[ClH:18].[N:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][NH2:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 113736-AminoquinolineHCID 61436Stannous chloride dihydrateHCID 23668193Sodium Nitrite

Product 1

HCID 534086886-Hydrazinylquinoline hydrochlorideYield 77%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

To a solution of quinolin-6-ylamine (5 g, 35 mmol) in conc. HCl (12 mL) was added dropwise an aqueous solution (4 mL) of NaNO2 (2.42 g, 35 mmol) at 0° C. The resulting mixture was stirred for 1 h and then treated dropwise with a solution of SnCl2.2H2O (15.8 g, 70 mmol) in conc. HCl (15 mL) at 0° C. The reaction mixture was stirred for 2 h at RT. The precipitate was collected and washed with EtOH and Et2O to yield 1-(quinolin-6-yl)hydrazine hydrochloride (4.3 g, 77% yield) as a yellow powder, which was used for the next reaction without further purification.

Workup

  1. stirringThe reaction mixture was stirred for 2 h at RT
  2. customThe precipitate was collected
  3. washwashed with EtOH and Et2O

Sources & evidence

ORD record
ord-fd397e935340468088a26f7eff50da59
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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