3-Aminoquinoline → 61621-35-0

HRID 1696478Notes

Reaction equation

HRID 1696478 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH2:11])[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][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][NH2:12])[CH:2]=1

Participants

5

Reactant 3

HCID 113753-AminoquinolineHCID 61436Stannous chloride dihydrateHCID 23668193Sodium Nitrite

Product 1

HCID 2048560061621-35-0Yield 81%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

To a solution of quinolin-3-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 with a solution of SnCl2.2H2O (15.8 g, 70 mmol) in conc. HCl (15 mL). The reaction solution was stirred for an additional 2 h at RT. The precipitate was filtered and washed with EtOH and ether to yield 1-(quinolin-3-yl)hydrazine hydrochloride (4.5 g, 81% yield), which was used in the next reaction without further purification.

Workup

  1. stirringThe reaction solution was stirred for an additional 2 h at RT
  2. filtrationThe precipitate was filtered
  3. washwashed with EtOH and ether

Sources & evidence

ORD record
ord-7506931bac304c28bf3083a28e8ab2ca
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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