Tetrafluoroboric acid → HCID 67214909, compound

HRID 2421528Notes

Reaction equation

HRID 2421528 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][C:6]=2N.N([O-])=O.[Na+].C1CCCCC1.C(OCC)(=O)C.[F:31][B-](F)(F)F.[H+]>O>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][C:6]=2[F:31]

Participants

6

Reactant 4

HCID 28118Tetrafluoroboric acidHCID 155690063-Bromo-6-methoxyquinolin-8-amineHCID 21867204Cyclohexane ethylacetateHCID 23668193Sodium Nitrite

Product 1

HCID 67214909HCID 67214909, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-bromo-6-methoxy-quinolin-8-ylamine (preparation described in Journal of Pharmaceutical Sciences (1984), 73(12), 1854-6) (5.0 g) in 20 ml fluoroboric acid, (50 wt % solution in water) at ˜5° C. was treated with a solution of sodium nitrite (1.9 g in 3 ml of water) over a period of 40 minutes. The reaction mixture was stirred at room temperature for 2 hours after which time the precipitate was filtered and washed with cold diethyl ether. The resulting brown powder was added portionwise to hot dichlorobenzene over 1.5 hours. Stirring was then continued for an additional 30 min at 190° C. On cooling to room temperature, the mixture was treated with dilute hydrochloric acid and diluted with ethyl acetate. The organic phase was washed with dilute sodium hydroxide, dried over sodium sulphate, filtered and evaporated under reduced pressure to give a black oil that was fractionated by chromatography (silica; cyclohexane/ethyl acetate) to give the required product (M+256)

Workup

  1. filtrationwas filtered
  2. washwashed with cold diethyl ether
  3. additionThe resulting brown powder was added portionwise to hot dichlorobenzene over 1.5 hours
  4. stirringStirring
  5. waitwas then continued for an additional 30 min at 190° C
  6. temperatureOn cooling to room temperature
  7. additionthe mixture was treated with dilute hydrochloric acid
  8. additiondiluted with ethyl acetate
  9. washThe organic phase was washed with dilute sodium hydroxide
  10. dry with materialdried over sodium sulphate
  11. filtrationfiltered
  12. customevaporated under reduced pressure
  13. customto give a black oil that

Sources & evidence

ORD record
ord-b6ed4bb16b214ce6aa5f5d7c3be9a519
Source dataset
uspto-grants-2011_06
Patent number
US07956188B2

Reaction notes

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