Tetrafluoroboric acid → HCID 18005020, compound

HRID 989058Notes

Reaction equation

HRID 989058 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[Cl:12])=[CH:9][C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[CH:6]=2.[H+].[B-:18]([F:22])([F:21])([F:20])[F:19].[N:23]([O-])=O.[Na+]>O1CCCC1.O>[F:19][B-:18]([F:22])([F:21])[F:20].[Cl:12][C:11]1[C:10]2[C:5](=[CH:6][C:7]([O:15][CH3:16])=[C:8]([O:13][CH3:14])[CH:9]=2)[N:4]=[CH:3][C:2]=1[N+:1]#[N:23]

Participants

6

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 22646632HCID 22646632, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 18005020HCID 18005020, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-amino-4-chloro-6,7-dimethoxyquinoline (3.3 g) was dissolved in tetrahydrofuran (70 ml) with stirring and then cooled in an ice/water bath to below 10° C. 48% aqueous fluoboric acid (7.3 ml) was then added and the mixture stirred for 5 minutes. A solution of sodium nitrite (1.05 g) in water (2 ml) was added keeping the temperature below 10° C. The reaction mixture was then stirred for 30 minutes with cooling. The resulting yellow solid was filtered off, washed with fresh tetrahydrofuran. Carefully vac dried. To give 4-chloro-6,7-dimethoxyquinoline-3-diazonium tetrafluoroborate (4.15 g, 89%).

Workup

  1. temperaturecooled in an ice/water bath to below 10° C
  2. stirringthe mixture stirred for 5 minutes
  3. customthe temperature below 10° C
  4. stirringThe reaction mixture was then stirred for 30 minutes
  5. temperaturewith cooling
  6. filtrationThe resulting yellow solid was filtered off
  7. washwashed with fresh tetrahydrofuran

Sources & evidence

ORD record
ord-32d5b572ba1b45ac9e7ada3fb38f61fa
Source dataset
uspto-grants-2003_10
Patent number
US06638945B1

Reaction notes

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