Methanol → HCID 178467690, compound

HRID 2290006Notes

Reaction equation

HRID 2290006 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][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][CH:23]([OH:25])[CH3:24])=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.CO.C#C>C(Cl)Cl.[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][CH:23]([OH:25])[CH3:24])=[CH:15][CH:14]=3)=[O:9])=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6326AcetyleneHCID 178467689HCID 178467689, compound

Product 1

HCID 178467690HCID 178467690, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-butynyl)-3-quinolinecarboxamide from Example No. 152 (106.3 mg) and Pd/C (10%, 21.3 mg) is dissolved in 40 mL 3:1 CH2Cl2 :MeOH. The reaction mixture is placed under the Parr hydrogenator at 34 psi H2 and monitored by mass spectroscopy for complete reduction of the acetylene. The old palladium catalyst is replaced with fresh palladium catalyst each time the reaction is taken off the Parr. In this case, the reaction is taken off the Parr twice. The reaction is complete in 130 min . The reaction mixture is filtered over celite to remove the palladium. The filtrate is condensed to obtain a solid. The crude product is adsorbed onto silica and chromatographed eluting with 4% MeOH in CH2Cl2. Fractions homogenous by TLC are combined and condensed to afford 30.0 mg (28%) of the title compound as a white solid.

Workup

  1. filtrationThe reaction mixture is filtered over celite
  2. customto remove the palladium
  3. customcondensed
  4. customto obtain a solid
  5. customchromatographed
  6. washeluting with 4% MeOH in CH2Cl2
  7. customcondensed

Sources & evidence

ORD record
ord-9fa0449c3a724b339476cc79194676af
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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