Water → HCID 69132345, compound

HRID 2370054Notes

Reaction equation

HRID 2370054 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[C:16]2[NH:21][C:20](=[O:22])[C:19](=[CH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[NH:18][C:17]2=[O:31])=[N:13][CH:14]=1)C1C=CC=CC=1.[OH-].[Na+].O>CO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[C:16]2[NH:21][C:20](=[O:22])[C:19](=[CH:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:18][C:17]2=[O:31])=[N:13][CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 69132355HCID 69132355, compound

Product 1

HCID 69132345HCID 69132345, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound B (0.5 g) and NaOH (0.5 g) were dissolved in 100 mL of methanol. The mixture was hydrogenated in the presence of 0.5 g of palladium/charcoal under 1 atmospheric pressure. After the completion of the reaction as monitored by TLC, the catalyst was removed by filtration and the filtrate was evaporated in vacuo to produce a residue, which was dissolved with 50 mL of water. The obtained aqueous solution was adjusted to PH=7. A precipitate was formed and collected to give a 0.27 g (70%) of 3-[(5-hydroxypyrid-in-2-yl)methylidene]-6-(benzylmethylidene)piperazine-2,5-dione (Compound C). 1H-NMR (400 MHz, CDCl3): 6.758 (s, 1H), 7.087 (s, 1H), 7.290-7.580 (m, 7H, aromatic), 8.328 (s, 1H), and 12.289 (s, 1H).

Workup

  1. customAfter the completion of the reaction
  2. customthe catalyst was removed by filtration
  3. customthe filtrate was evaporated in vacuo
  4. customto produce a residue, which
  5. customA precipitate was formed
  6. customcollected

Sources & evidence

ORD record
ord-fdfc626af01d45509230dc872c919a6e
Source dataset
uspto-grants-2014_04
Patent number
US08710062B2

Reaction notes

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