1-(4'Fluorophenyl) amino-2-cyano-3,4-dihydro-naphthalene → 7-Amino-9-fluoro-5,6-dihydrobenz[c] acridine

HRID 366403Notes

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]2

Participants

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.

Workup

temperatureAfter cooling
temperaturethe mixture heated
temperatureunder reflux for 1 hour
temperatureto cool
filtrationthis mixture was filtered
washthe solid washed with dichloromethane
extractionAny organics in the filtrate were also extracted into dichloromethane
extractionAll extractions
dry with materialdried (Na2SO4)
filtrationfiltered
customthe solvent evaporated
distillationKugelrohr distillation (210° C., 0.07 mmHg)

Sources & evidence

ORD record: ord-4adb63c04d6b4fbe8c87e4a9444c35a5
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130228

Reaction notes

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