Hydrogen Bromide → HCID 18415758, compound

HRID 990751Notes

Reaction equation

HRID 990751 reaction equation
[ClH:1].C[O:3][C:4]1[CH:5]=[CH:6][C:7]2[CH:8]3[CH2:16][CH:12]([CH2:13][C:14]=2[CH:15]=1)[CH2:11][NH:10][CH2:9]3.Br.[NH4+].[OH-]>>[ClH:1].[CH:8]12[CH2:16][CH:12]([CH2:11][NH:10][CH2:9]1)[CH2:13][C:14]1[CH:15]=[C:4]([OH:3])[CH:5]=[CH:6][C:7]2=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 14923Ammonium HydroxideHCID 18415751HCID 18415751, compound

Product 1

HCID 18415758HCID 18415758, compoundYield 40%

Procedure

5-Methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene hydrochloride (187 mg, 0.78 mmol) was brought to reflux in 48%HBr (5 mL). After 1 hour the solution was cooled and poured into aq. NH4OH soln., the pH was adjusted to ˜9 and the product was extracted with EtOAc (3×40 mL). The organic layer was washed with brine (50 mL), dried (MgSO4) and concentrated to a solid. (TLC 10%MeOH/CH2Cl2 (NH3) Rf 0.13). This material was dissolved in excess 1N HCl MeOH and concentrated. Recrystallization from MeOH/Et2O provided a solid (70 mg, 40%). 1H NMR (CD3OD) δ6.99 (d, J=8.0 Hz, 1H), 6.63 (m, 2H), 3.48-3.11 (6H), 2.83 (d, J=18.0 Hz, 1H), 2.42 (br s, 1H), 2.08 (AB d, J=12.5 Hz, 1H), 1.93 (AB d, J=12.5 Hz, 1H). mp 295-298° C.

Workup

  1. temperatureAfter 1 hour the solution was cooled
  2. extractionthe product was extracted with EtOAc (3×40 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to a solid
  6. dissolutionThis material was dissolved in excess 1N HCl MeOH
  7. concentrationconcentrated
  8. customRecrystallization from MeOH/Et2O

Sources & evidence

ORD record
ord-336ea31f66294f5cb74211066d358b1f
Source dataset
uspto-grants-2002_10
Patent number
US06462035B1

Reaction notes

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