Iodoethane → (4aR)-(10bR)-8-chloro-4-ethyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

HRID 1901990Notes

Reaction equation

HRID 1901990 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[C@@H:6]3[C@@H:11]([CH2:12][CH2:13][C:4]=2[CH:3]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]3.[OH-].[Na+].[CH2:19](I)[CH3:20]>C1COCC1>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[C@@H:6]3[C@@H:11]([CH2:12][CH2:13][C:4]=2[CH:3]=1)[N:10]([CH2:19][CH3:20])[C:9](=[O:14])[CH2:8][CH2:7]3

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 100599928-Chloro-1,4,4a,5,6,10b-hexahydro-2H-benzo[f]quinolin-3-one

Product 1

HCID 54421716(4aR)-(10bR)-8-chloro-4-ethyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 9.4 g portion of (4aR)-(10bR)-8-chloro-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one was combined in a flask with 94 ml of THF, 20 mL of 50% aqueous sodium hydroxide and 9.36 g of ethyl iodide, and was stirred at reflux, about 66°, for about 16 hours. The mixture was cooled to ambient temperature, and the layers were separated. The organic layer was evaporated to an oil, which was dissolved in ethyl acetate and extracted three times with 100 mL portions of water. It was then dried and evaporated to half its volume while heptane was added in portions. The resulting white crystalline product was filtered, washed with heptane and dried under vacuum at 25° to obtain 3.15 g of the desired product, m.p. 108°-110°. Analysis calculated for C15H18ClNO: C, 68.54; H, 6.83; N, 5.54 Found: C, 68.50; H, 6.88; N, 5.31

Workup

  1. temperatureat reflux, about 66°, for about 16 hours
  2. customthe layers were separated
  3. customThe organic layer was evaporated to an oil, which
  4. dissolutionwas dissolved in ethyl acetate
  5. extractionextracted three times with 100 mL portions of water
  6. customIt was then dried
  7. customevaporated to half its volume while heptane
  8. additionwas added in portions
  9. filtrationThe resulting white crystalline product was filtered
  10. washwashed with heptane
  11. customdried under vacuum at 25°

Sources & evidence

ORD record
ord-0043f538c58b41c984f24fdc7ff95ff2
Source dataset
uspto-grants-1996_11
Patent number
US05578724

Reaction notes

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