3-Aminoquinoline → HCID 21155575, compound

HRID 2249867Notes

Reaction equation

HRID 2249867 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[N:12]([O-])=O.[Na+].F[B-](F)(F)F.[H+]>Cl.O>[N+:1](=[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]2)=[N:4][CH2:3]1)=[N-:12]

Participants

6

Reactant 3

HCID 113753-AminoquinolineHCID 28118Tetrafluoroboric acidHCID 23668193Sodium Nitrite

Product 1

HCID 21155575HCID 21155575, compoundYield 140.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

3-Aminoquinoline (10 g, 69 mmol) was dissolved in 70 mL of conc. HCl in a 250 mL round bottomed flask and cooled to 0° C. Sodium nitrite (9.6 g, 139 mmol) in 20 mL water was added drop wise over 0.5 h while maintaining the reaction temperature between 0-5° C. After stirring for another 0.5 h, fluoroboric acid (20 mL) was added and the stirring continued for another 0.5 h. The solid was filtered and dried under vacuum to yield the title compound (15.2 g, 90%).

Workup

  1. temperaturewhile maintaining the reaction temperature between 0-5° C
  2. waitthe stirring continued for another 0.5 h
  3. filtrationThe solid was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-fa3a085753ee491cbfed86a7cff36021
Source dataset
uspto-grants-2008_01
Patent number
US07314939B2

Reaction notes

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