HCID 20228695, compound → HCID 20228735, compound

HRID 1731362Notes

Reaction equation

HRID 1731362 reaction equation
C([O:8][C:9]1[C:10]2[N:11]([C:15]([CH3:29])=[C:16]([C:18]3[CH:19]=[CH:20][C:21]4[O:25][C:24](=[O:26])[N:23]([CH3:27])[C:22]=4[CH:28]=3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[H][H]>C(O)C.O1CCCC1.[Pd]>[OH:8][C:9]1[C:10]2[N:11]([C:15]([CH3:29])=[C:16]([C:18]3[CH:19]=[CH:20][C:21]4[O:25][C:24](=[O:26])[N:23]([CH3:27])[C:22]=4[CH:28]=3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 2

HCID 20228695HCID 20228695, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20228735HCID 20228735, compoundYield 63.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(8-benzyloxy-3-methylimidazo[1,2-a]pyridin-2-yl)-3-methyl-2-benzoxazolinone (1.6 g) in a mixture of ethanol (200 ml) and tetrahydrofuran (100 ml) was hydrogenated over 10% palladium on carbon (wet, 0.5 g) under an atmospheric pressure of hydrogen at ambient temperature for an hour. The catalyst and an insoluble material were filtered off and the filtrate was evaporated in vacuo. The residue was recrystallized from a mixture of tetrahydrofuran and ethanol to give 5-(8-hydroxy-3-methylimidazo[1,2-a]pyridin-2-yl)-3-methyl-2-benzoxazolinone (0.78 g). mp. >280° C.

Workup

  1. filtrationThe catalyst and an insoluble material were filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was recrystallized from a mixture of tetrahydrofuran and ethanol

Sources & evidence

ORD record
ord-881a0eb97db44b7995636447c18dd973
Source dataset
uspto-grants-1986_11
Patent number
US04621084

Reaction notes

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