SMR000102306 → 1H-Cyclopenta(b)quinoline, 2,3-dihydro-9-amino-7-bromo-

HRID 366395Notes

Reaction equation

HRID 366395 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]=12

Participants

4

Reactant 1

HCID 622051SMR000102306

Product 1

HCID 30413501H-Cyclopenta(b)quinoline, 2,3-dihydro-9-amino-7-bromo-

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 14798Sodium HydroxideSolvent

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.

Workup

  1. temperatureAfter cooling
  2. temperaturethe mixture heated
  3. temperatureunder reflux for 1 hour
  4. temperatureto cool
  5. filtrationthis mixture was filtered
  6. washthe solids washed with dichloromethane
  7. extractionAny organics in the filtrate were also extracted into dichloromethane
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customthe solvent evaporated
  11. distillationKugelrohr distillation (180° C., 0.04 mmHg)

Sources & evidence

ORD record
ord-2e4ec425ea4c498ab9a30c28042701d1
Source dataset
uspto-grants-2000_10
Patent number
US06130228

Reaction notes

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