Quinoline → HCID 53966698, compound

HRID 596943Notes

Reaction equation

HRID 596943 reaction equation
N1C2C(=CC=CC=2)C=CC=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([OH:39])[C:19]#[C:20][CH2:21][N:22]2[CH2:38][CH2:37][C:25]3([N:29]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:28][NH:27][C:26]3=[O:36])[CH2:24][CH2:23]2)=[CH:14][CH:13]=1.[H][H]>[Pd].C(O)C.C(Cl)(Cl)Cl>[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([OH:39])[CH:19]=[CH:20][CH2:21][N:22]2[CH2:38][CH2:37][C:25]3([N:29]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH2:28][NH:27][C:26]3=[O:36])[CH2:24][CH2:23]2)=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 7047QuinolineHCID 21449413HCID 21449413, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53966698HCID 53966698, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent2×HCID 6212ChloroformSolvent

Procedure

To a deactivated palladium catalyst, which was prepared from 5% palladium on barium sulfate (30 mg) and quinoline (15 mg) in ethanol (6 ml) and chloroform (2 ml) by stirring for 15 minutes under hydrogen, was added a solution of 8-[4(p-fluorophenyl)-4-hydroxy-2-butynyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one (0.80 g) in ethanol (3 ml), and the resulting mixture was stirred under hydrogen at 25° C until an equimolar amount of hydrogen (48 ml) was consumed. The catalyst was filtered off, and the filtrate was concentrated in vacuum and chromatographed to afford 8-[4(p-fluorophenyl)-4-hydroxy-2-butenyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one as oily materials. νC=Oneat 1700 cm-1.

Workup

  1. customwas consumed
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated in vacuum
  4. customchromatographed

Sources & evidence

ORD record
ord-1a4d80621bdd4d1d85488d1557fe5d99
Source dataset
uspto-grants-1977_03
Patent number
US04012514

Reaction notes

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