Acetic Acid → HCID 18788592, compound

HRID 263950Notes

Reaction equation

HRID 263950 reaction equation
[CH:1]1([C:7]#[C:8][C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([O:19][CH3:20])=[C:14]([O:21][CH3:22])[CH:13]=3)[CH2:6][CH2:5][CH2:4]CC1.[C:23](O)(=O)[CH3:24]>CO.[Pd]>[CH:8]1([C:9]2[C:10]([CH2:23][CH3:24])=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([O:19][CH3:20])=[C:14]([O:21][CH3:22])[CH:13]=3)[CH2:4][CH2:5][CH2:6][CH2:1][CH2:7]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 10402251HCID 10402251, compound

Product 1

HCID 18788592HCID 18788592, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 3-cyclohexylethynyl-6,7-dimethoxyquinoline (215 mg; 0.73 mmol) in 10 mL CH3OH and 20 mL glacial acetic acid is added 22 mg 10% Pd/C. H2 is bubbled through the reaction mixture and then filtered, evaporated to dryness and diluted with distilled water. This is then neutralized with Na2CO3, extracted with EtOAc, washed with brine, dried (MgSO4), evaporated to dryness and chromatographed with 8:2/hexane: EtOAc to obtain 3-cyclohexyl-ethyl-6,7- dimethoxyquinoline.

Workup

  1. customH2 is bubbled through the reaction mixture
  2. filtrationfiltered
  3. customevaporated to dryness
  4. additiondiluted with distilled water
  5. extractionextracted with EtOAc
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness
  9. customchromatographed with 8:2/hexane

Sources & evidence

ORD record
ord-527c7ef370474d39b50b5e8458286b10
Source dataset
uspto-grants-1997_07
Patent number
US05646153

Reaction notes

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