Hydrochloric Acid → 6-Hydrazinylquinoline hydrochloride

HRID 1930330Notes

Reaction equation

HRID 1930330 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.Cl.[N:13]([O-])=O.[Na+].O.O.[Cl:19][Sn]Cl>>[ClH:19].[N:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][NH2:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 113736-AminoquinolineHCID 61436Stannous chloride dihydrateHCID 23668193Sodium Nitrite

Product 1

HCID 534086886-Hydrazinylquinoline hydrochlorideYield 77%

Procedure

To a solution of quinolin-6-ylamine (5 g, 35 mmol) in cone. 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 cone. 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. customat 0° C
  2. stirringThe reaction mixture was stirred for 2 h at RT
  3. customThe precipitate was collected
  4. washwashed with EtOH and Et2O

Sources & evidence

ORD record
ord-f028211c3b0b49aba931e772314a4355
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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