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

HRID 1780372Notes

Reaction equation

HRID 1780372 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 with 150 mL of THF, 20 mL of 50% aqueous sodium hydroxide and 12.5 g of ethyl iodide in a flask, and was warmed with stirring to about 37°. Stirring at approximately constant temperature was continued for about 72 hours and the reaction was worked up as described above in Example 2 to obtain 3.88 g of the desired product, m.p. 108°-110°. The product was found to be 98.6% pure by HPLC, eluting with 1:1 acetonitrile:aqueous buffer (5% ammonium acetate) and monitoring at 220 nanometers.

Workup

  1. temperaturewas warmed
  2. stirringStirring at approximately constant temperature

Sources & evidence

ORD record
ord-e728152b9f604951806bcfa720b8446f
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

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