Tetrafluoroboric acid → HCID 22284860, compound

HRID 1061518Notes

Reaction equation

HRID 1061518 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[NH2:24].[H+].[B-:26]([F:30])([F:29])([F:28])[F:27].[N:31]([O-])=O.[Na+]>C1COCC1.O>[F:27][B-:26]([F:30])([F:29])[F:28].[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:24]#[N:31]

Participants

6

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 22284885HCID 22284885, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22284860HCID 22284860, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-chloro-6-methoxy-7-(3-piperidin-1-yl-propoxy)-quinolin-3-ylamine (0.300 g) was dissolved in THF (5 ml) with stirring and then cooled in ice-water bath to below 0° C., to this added 48% aqueous fluoboric acid (0.7 ml) and mixture stirred for 10 mins. A solution of sodium nitrite (0.10 sg) in water (1 ml) was added keeping the temperature below 10° C. The reaction mixture was the stirred for 1 hr, during that time yellow solid precipitated. This solid was filtered, dried to give 4-chloro-6-methoxy-7-(3-piperidin-1-yl-propoxy)-quinolin-3-diazonium tetrafluoroborate (0.250 g, 80%)

Workup

  1. customthe temperature below 10° C
  2. stirringstirred for 1 hr, during that time yellow solid
  3. customprecipitated
  4. filtrationThis solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-55edef43e58342a7967b0db61da4bc6a
Source dataset
uspto-grants-2005_11
Patent number
US06960580B2

Reaction notes

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