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

HRID 1857978Notes

Reaction equation

HRID 1857978 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 2520 to obtain 3.15 g of the desired product, m.p. 108-110°.

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 2520

Sources & evidence

ORD record
ord-e2a31a2c33724f359a3f56f728ed9d1c
Source dataset
uspto-grants-2000_11
Patent number
US06150375

Reaction notes

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