6-Aminoquinoline → 6-Hydrazinylquinoline hydrochloride

HRID 1696476Notes

Reaction equation

HRID 1696476 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+].[Cl:16][Sn]Cl>Cl>[ClH:16].[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 24479Stannous ChlorideHCID 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 as a yellow powder (4.3 g, 77% yield), 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-d1191acf4035479f97501a460505b2a1
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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