5-Ethyl-4-[(4-methoxyphenyl)sulfonyl]-2-vinyl4,5-dihydrothieno[3,2-c]isoquinoline → 2,5-Diethyl-4-[(4-methoxyphenyl)sulfonyl]-4,5-dihydrothieno[3,2-c]isoquinoline

HRID 641634Notes

Reaction equation

HRID 641634 reaction equation
[CH2:1]([CH:3]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:6]2[S:13][C:14]([CH:16]=[CH2:17])=[CH:15][C:5]=2[N:4]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:16]([C:14]1[S:13][C:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[CH:3]([CH2:1][CH3:2])[N:4]([S:18]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)(=[O:20])=[O:19])[C:5]=2[CH:15]=1)[CH3:17]

Participants

4

Reactant 1

HCID 586693955-Ethyl-4-[(4-methoxyphenyl)sulfonyl]-2-vinyl4,5-dihydrothieno[3,2-c]isoquinoline

Product 1

HCID 586693972,5-Diethyl-4-[(4-methoxyphenyl)sulfonyl]-4,5-dihydrothieno[3,2-c]isoquinolineYield 87.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-ethyl-4-[(4-methoxyphenyl)sulfonyl]-2-vinyl4,5-dihydrothieno[3,2-c]isoquinoline (1.44 g, 3.50 mmol) in ethyl acetate (35 mL) was hydrogenated over 10% palladium-on-carbon (0.29 g) at 23° C. and 1 atm. After 1 h the catalyst was filtered (Celite), washed with ethyl acetate (35 mL), and the filtrate was concentrated in vacuo to give the crude product (1.37 g) as a pale yellow solid. Recrystallization from boiling hexane provided the title compound (1.26 g, 87%, m.p. 105.0-105.5° C.) as shiny pale yellow needles.

Workup

  1. filtrationAfter 1 h the catalyst was filtered (Celite)
  2. washwashed with ethyl acetate (35 mL)
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give the crude product (1.37 g) as a pale yellow solid
  5. customRecrystallization

Sources & evidence

ORD record
ord-b444bacaf13f4d1fb3c86b6288d5e52e
Source dataset
uspto-grants-2010_04
Patent number
US07696221B2

Reaction notes

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