1-(4'Fluorophenyl) amino-2-cyano-3,4-dihydro-naphthalene → 7-Amino-9-fluoro-5,6-dihydrobenz[c] acridine
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][C:10]=2[C:19]#[N:20])=[CH:4][CH:3]=1>[Ti](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>[NH2:20][C:19]1[C:10]2[CH2:11][CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:9]=2[N:8]=[C:5]2[C:6]=1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4]2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 140 °C
Procedure
Under nitrogen, titanium tetrachloride (0.3 ml, 2.7 mmol) was added to the above enamine (Example 36) (0.65 g, 2.5 mmol) and the stirred mixture was heated at 140° C. for 1 hour. After cooling, 10M-sodium hydroxide (20 ml) was added and the mixture heated under reflux for 1 hour After being allowed to cool, this mixture was filtered and the solid washed with dichloromethane. Any organics in the filtrate were also extracted into dichloromethane. All extractions were combined, dried (Na2SO4), filtered and the solvent evaporated. Kugelrohr distillation (210° C., 0.07 mmHg) gave the product as a pale yellow powder.