Sodium Hydroxide → 11-Aza-tricyclo[7.3.1.0*2,7*]trideca-2,4,6-trien-6-ol
Reaction equation
Cl.C[O:3][C:4]1[C:15]2[CH2:14][CH:13]3[CH2:16][CH:9]([CH2:10][NH:11][CH2:12]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1.[OH-].[Na+]>>[CH:9]12[CH2:16][CH:13]([CH2:12][NH:11][CH2:10]1)[CH2:14][C:15]1[C:4]([OH:3])=[CH:5][CH:6]=[CH:7][C:8]2=1Participants
3
Procedure
6-Methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene hydrochloride (55 mg, 0.23 mmol) was brought to reflux in 48% aq. hydrobronic acid (HBr) (5 mL). After 1 hour the solution was cooled and poured into 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 EtOAc/hexanes (20 mg, 46%). 1H NMR (CDCl3) δ6.95 (t, J=8.0 Hz, 1H), 6.68 (d, J=8.0 Hz, 1H), 6.53 (d, J=8.0 Hz, 1H), 3.27 (m, 1H), 3.11 (m, 2H), 3.02 (m, 2H), 2.77 (m, 1H), 2.57 (m, 1H), 2.33 (br s, 1H), 1.90 (m, 2H). mp 106-108° C.
Workup
- temperatureAfter 1 hour the solution was cooled
- extractionwas extracted with EtOAc (3×40 mL)