Methyl iodide → 8-Bromo-4-methyl-1,2,3,4,5,6-hexahydrobenzo[f]quinolin-3-one

HRID 1655299Notes

Reaction equation

HRID 1655299 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]3[CH2:7][CH2:8][C:9](=[O:14])[NH:10][C:11]=3[CH2:12][CH2:13][C:4]=2[CH:3]=1.N1C2C(CCC3C=CC=CC=32)CC[C:18]1=O.[H-].[Na+].CI>C(OCC)C.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]3[CH2:7][CH2:8][C:9](=[O:14])[N:10]([CH3:18])[C:11]=3[CH2:12][CH2:13][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 197073228-bromo-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-oneHCID 70192667Hexahydrobenzoquinolinone

Product 1

HCID 229095038-Bromo-4-methyl-1,2,3,4,5,6-hexahydrobenzo[f]quinolin-3-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 22728543Water ethylacetateSolvent

Procedure

By substantially following the procedures described above in Example 1 5.17 g of 8-bromo-1,2,3,4,5,6-hexahydrobenzo[f]quinolin-3-one was obtained. The hexahydrobenzoquinolinone (5.17 g; 19.6 mmol) was dissolved in 60 ml of dry diethyl ether in a 250 ml round bottomed flask. To the solution was added 1.2 g of sodium hydride (60% dispersion in mineral oil). The flask was fitted to a reflux condenser with a stirring bar and the mixture refluxed for 2 hours. The mixture was then cooled to room temperature and 7.35 ml of methyl iodide was added. After addition, the reaction mixture was refluxed for an additional 3 hours. After cooling, the reaction mixture was quenched by the cautious addition of 5 ml of water. The mixture was then concentrated under vacuum affording a pale solid which was taken up in a ethyl acetate/water mixture and the resulting layers separated. The organic layer was washed twice with water and once with brine and then dried over MgSO4 and concentrated under vacuum to afford 5.22 g of a yellow crystalline solid. The solid was recrystallized from acetone to afford 3.55 g (62%) of the subtitle compound as a pale yellow solid. Melting point 126°-128° C.

Workup

  1. customwas obtained
  2. customThe flask was fitted to a reflux condenser with a stirring bar
  3. temperaturethe mixture refluxed for 2 hours
  4. additionAfter addition
  5. temperaturethe reaction mixture was refluxed for an additional 3 hours
  6. temperatureAfter cooling
  7. customthe reaction mixture was quenched by the cautious addition of 5 ml of water
  8. concentrationThe mixture was then concentrated under vacuum
  9. customaffording a pale solid which
  10. customthe resulting layers separated
  11. washThe organic layer was washed twice with water and once with brine
  12. dry with materialdried over MgSO4
  13. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c3176a1c08844a2bac0aa57b15141201
Source dataset
uspto-grants-1993_10
Patent number
US05250539

Reaction notes

Loading…