Quinoline → HCID 86733440, compound

HRID 1076869Notes

Reaction equation

HRID 1076869 reaction equation
[O:1]=[C:2]([CH2:9][CH2:10][C:11]#[C:12][CH:13]([OH:18])[CH:14]([Cl:17])[CH2:15][CH3:16])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].N1C2C(=CC=CC=2)C=CC=1>C(OCC)(=O)C.[Pd]>[O:1]=[C:2]([CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH:13]([OH:18])[CH:14]([Cl:17])[CH2:15][CH3:16])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 7047QuinolineHCID 21538704HCID 21538704, compound

Product 1

HCID 86733440HCID 86733440, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4.6 g of the product of Step A in 66 ml of ethyl acetate containing 0.5 g of 5% palladium on barium sulfate and 0.625 ml of quinoline was hydrogenated and then was filtered to remove the catalyst. The filtrate was washed with dilute hydrochloric acid and then with water, was dried and evaporated to dryness to obtain 4.6 g of ethyl 3-oxo-8-hydroxy-9-chloro-cis-6-undecenoate with a refractive index of nD20 = 1.4800.

Workup

  1. filtrationwas filtered
  2. customto remove the catalyst
  3. washThe filtrate was washed with dilute hydrochloric acid
  4. dry with materialwith water, was dried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-afc52f68b80a4015a050d81af7e652e0
Source dataset
uspto-grants-1976_05
Patent number
US03958005

Reaction notes

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