Acetic Acid → HCID 18788592, compound

HRID 374473Notes

Reaction equation

HRID 374473 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 10mL 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-25562d993a584050bf44fcfb4513c2da
Source dataset
uspto-grants-1996_01
Patent number
US05480883

Reaction notes

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