Hydrogen Bromide → 11-Aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-OL

HRID 990755Notes

Reaction equation

HRID 990755 reaction equation
Cl.C[O:3][C:4]1[CH:15]=[CH:14][C:13]2[CH2:12][CH:11]3[CH2:16][CH:7]([CH2:8][NH:9][CH2:10]3)[C:6]=2[CH:5]=1.Br.[OH-].[Na+]>>[CH:7]12[CH2:16][CH:11]([CH2:10][NH:9][CH2:8]1)[CH2:12][C:13]1[CH:14]=[CH:15][C:4]([OH:3])=[CH:5][C:6]2=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 184157334-Methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene hydrochloride

Product 1

HCID 1021974811-Aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-OL

Procedure

4-Methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene hydrochloride (120 mg, 0.50 mmol) was brought to reflux in 48%HBr (2 mL). After 1 hour the solution was cooled and poured Into a 1N aq. NaOH soln. adjusted to pH 10 and product was extracted with EtOAc (3×40 mL). The organic layer was washed with brine (50 mL), dried (MgSO4) and concentrated to a white solid which was recrystallized from Et2O/hexanes (40 mg, 42%). (TLC 50%EtOAc/CH2Cl2 Rf 0.15). 1H NMR (CDCl3) δ6.96 (d, J=8.0 Hz, 1H), 6.60 (dd, J=8.0,2.5 Hz, 1H), 6.46 (d, J=2.5 Hz, 1H), 3.31 (m, 1H), 3.03 (dd, J=17.0,6.0 Hz, 1H), 2.95 (m, 2H,NH), 2.73 (m, 3H), 1.99 (m, 2H), 1.87 (AB d, J=12.5 Hz, 1H). mp 215-217° C.

Workup

  1. temperatureAfter 1 hour the solution was cooled
  2. extractionwas 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 white solid which
  6. customwas recrystallized from Et2O/hexanes (40 mg, 42%)

Sources & evidence

ORD record
ord-9cdcfc9821914ba88c5dcade9369df4e
Source dataset
uspto-grants-2002_10
Patent number
US06462035B1

Reaction notes

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