3-Aminoquinoline → HCID 21155575, compound

HRID 549210Notes

Reaction equation

HRID 549210 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-4e77f0116d8a4b6d88423137e2c929b9
Source dataset
uspto-grants-2011_05
Patent number
US07943640B2

Reaction notes

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