HCID 10402251, compound → HCID 10040402, compound

HRID 1654679Notes

Reaction equation

HRID 1654679 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][CH2:3][CH2:2]1>CO.C(O)(=O)C.[Pd]>[CH:1]1([CH2:7][CH2:8][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][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 10402251HCID 10402251, compound

Product 1

HCID 10040402HCID 10040402, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 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-cyclohexylethyl-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-b198e0da133d42828f8e377a8506cd45
Source dataset
uspto-grants-1995_04
Patent number
US05409930

Reaction notes

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