SMR000102306 → 1H-Cyclopenta(b)quinoline, 2,3-dihydro-9-amino-7-bromo-
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH2:13][CH2:12][CH2:11][C:10]=2[C:14]#[N:15])=[CH:4][CH:3]=1>[Ti](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>[NH2:15][C:14]1[C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=2[N:8]=[C:9]2[CH2:13][CH2:12][CH2:11][C:10]=12Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 140 °C
Procedure
Under nitrogen, titanium tetrachloride (1.2 ml, 11 mmol) was added to the above enamine (Example 22) (2.6 g, 20 mmol) and the stirred mixture was heated at 140° C. for 1 hour. After cooling, 10M-sodium hydroxide solution (20 ml) was added and the mixture heated under reflux for 1 hour. After being allowed to cool, this mixture was filtered and the solids washed with dichloromethane. Any organics in the filtrate were also extracted into dichloromethane. All extracts were combined, dried (Na2SO4), filtered and the solvent evaporated. Kugelrohr distillation (180° C., 0.04 mmHg) gave the product as a pale yellow powder.