HCID 178522892, compound → HCID 178522866, compound

HRID 2289947Notes

Reaction equation

HRID 2289947 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=[CH:17][C:16]=3Cl)=[O:11])=[CH:4][CH:3]=1>C(O)(=O)C.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=[CH:17][CH:16]=3)=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 178522892HCID 178522892, compound

Product 1

HCID 178522866HCID 178522866, compoundYield 3.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
190 °C

Procedure

N-((4-Chlorophenyl)methyl)-8-chloro-4-hydroxy-5-trifluromethyl-3-quinoline-carboxamide (2.00 g) from Example No. 59 is dissolved in glacial acetic acid (100 mL) along with NaOAc·3H2O (937 mg) and 5% palladium on carbon (666 mg). The mixture is placed under hydrogen pressure (25 psi) in a Parr hydrogenator for 3 h. The reaction mixture is filtered through a plug of celite, concentrated, suspended in water (30 mL), and filtered. The resulting solid (500 mg) and 4-chlorobenzylamine (2.13 mL) are then heated at 190° C. for 1 h. The crude product is purified by column chromatography (dichloromethane/methane, 50/1) to afford 62 mg of the title compound as a white solid.

Workup

  1. customfor 3 h
  2. filtrationThe reaction mixture is filtered through a plug of celite
  3. concentrationconcentrated
  4. filtrationfiltered
  5. customThe crude product is purified by column chromatography (dichloromethane/methane, 50/1)

Sources & evidence

ORD record
ord-a4568207f92e40d785b4acaed0042546
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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