Sodium Hydroxide → HCID 22254631, compound

HRID 1611679Notes

Reaction equation

HRID 1611679 reaction equation
[CH3:1][CH:2]([O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([NH2:17])[CH:13]=[CH:12]2)[CH2:3][CH:4]=[CH2:5].B.C1C[O:22]CC1.[OH-].[Na+]>OO>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[C:7]([O:6][CH:2]([CH3:1])[CH2:3][CH2:4][CH2:5][OH:22])[CH:8]=[CH:9][CH:10]=2)[N:15]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 22254598HCID 22254598, compound

Product 1

HCID 22254631HCID 22254631, compound

Reagents, catalysts & solvents 1

HCID 784Hydrogen PeroxideSolvent

Procedure

To a 100 mL round bottom flask containing 1.33 g (5.83 mmol) of 8-(1-methyl-but-3-enyloxy)-quinolin-2-ylamine was added 30 mL of a 1M solution of BH3/THF via syringe. Following the addition, the flask was fitted with a reflux condenser and the solution heated to reflux under N2 for 6 h. The reaction mixture was then allowed to cool to room temperature and the volatiles were removed in vacuo. The residue was dissolved in Et2O. Following the addition of 2.25 g (56.2 mmol) of solid NaOH, the mixture was placed in an ice bath. The flask was then fitted with a dropping funnel and 10 mL of 20% aqueous H2O2 was added dropwise with stirring. The funnel was then replaced with a reflux condenser and the mixture heated to reflux with stirring overnight. The resulting suspension was allowed to cool to room temperature and was filtered through a fritted funnel. The ethereal layer was separated, washed thoroughly with 1 M NaHSO4, dried over anhydr. Na2SO4 and evaporated in vacuo. The resulting crude material was purified by silica gel column chromatography (5–25% MeOH/CH2Cl2) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.82 (d, 1H), 7.16 (m, 1H), 7.03 (m, 1H), 6.97 (m, 1H), 6.73 (d, 1H), 6.33 (s, 1H), 4.62 (m, 1H), 4.46 (m, 1H), 3.44 (m, 2H), 1.76 (m, 1H), 1.59 (m, 3H), 1.27 (d, 3H); MS (DCI/NH3) m/z 247 [M+H]+.

Workup

  1. additionthe addition
  2. customthe flask was fitted with a reflux condenser
  3. temperaturethe solution heated
  4. temperatureto reflux under N2 for 6 h
  5. customthe volatiles were removed in vacuo
  6. dissolutionThe residue was dissolved in Et2O
  7. customthe mixture was placed in an ice bath
  8. customThe flask was then fitted with a dropping funnel
  9. customThe funnel was then replaced with a reflux condenser
  10. temperaturethe mixture heated
  11. temperatureto reflux
  12. stirringwith stirring overnight
  13. temperatureto cool to room temperature
  14. filtrationwas filtered through a fritted funnel
  15. customThe ethereal layer was separated
  16. washwashed thoroughly with 1 M NaHSO4
  17. customdried over anhydr
  18. customNa2SO4 and evaporated in vacuo
  19. customThe resulting crude material was purified by silica gel column chromatography (5–25% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-8d2f9c7bff304235bbfa822c802e2985
Source dataset
uspto-grants-2006_01
Patent number
US06989392B2

Reaction notes

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