Methanol → HCID 178522862, compound

HRID 2289996Notes

Reaction equation

HRID 2289996 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([C:21]#[C:22][CH2:23][OH:24])=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.CO.C#C>C(Cl)Cl.CCOCC.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][CH2:22][CH2:23][OH:24])=[CH:15][CH:14]=3)=[O:9])=[CH:25][CH:26]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 6326AcetyleneHCID 178522861HCID 178522861, compound

Product 1

HCID 178522862HCID 178522862, compoundYield 14%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Example No. 134 (231.0 mg) and Pd/C (10%, 46.2 mg) are dissolved in 40 mL 3:1 CH2Cl2 :MeOH. The reaction mixture is placed under the Parr hydrogenator at 26 psi and monitored with the OAMS for complete reduction of the acetylene. The reaction is complete in 25 min and filtered over celite to remove the palladium. The filtrate is condensed to obtain a solid. The solid is suspended in ether, filtered, and collected to yield 31.8 mg (14%) of the desired product as a white solid.

Workup

  1. filtrationfiltered over celite
  2. customto remove the palladium
  3. customcondensed
  4. customto obtain a solid
  5. filtrationfiltered
  6. customcollected

Sources & evidence

ORD record
ord-d9902c56edd94664bd53c528bced87a1
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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