5-carboxy-2,3,5,8-tetrahydro-1,3-dioxo-1H-1,2,4-triazolo[1,2-a]pyridazine-2-acetic acid → 5-carboxy2,3,5,6,7,8-hexahydro-1,3-dioxo-1H-1,2,4-triazolo[1,2-a]pyridazine-2-acetic acid

HRID 1660128Notes

Reaction equation

HRID 1660128 reaction equation
[C:1]([CH:4]1[CH:9]=[CH:8][CH2:7][N:6]2[C:10](=[O:18])[N:11]([CH2:14][C:15]([OH:17])=[O:16])[C:12](=[O:13])[N:5]12)([OH:3])=[O:2]>O1CCOCC1.[Pd]>[C:1]([CH:4]1[CH2:9][CH2:8][CH2:7][N:6]2[C:10](=[O:18])[N:11]([CH2:14][C:15]([OH:17])=[O:16])[C:12](=[O:13])[N:5]12)([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 205575155-carboxy-2,3,5,8-tetrahydro-1,3-dioxo-1H-1,2,4-triazolo[1,2-a]pyridazine-2-acetic acid

Product 1

HCID 205575025-carboxy2,3,5,6,7,8-hexahydro-1,3-dioxo-1H-1,2,4-triazolo[1,2-a]pyridazine-2-acetic acidYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumSolventHCID 312751,4-DioxaneSolvent

Procedure

0.75 g of 5-carboxy-2,3,5,8-tetrahydro-1,3-dioxo-1H-1,2,4-triazolo[1,2-a]pyridazine-2-acetic acid was dissolved in 50 ml of dioxan and hydrogenated in the presence of 10% palladium-on-charcoal at room temperature for 3 hours. The catalyst was filtered off and the filtrate was evaporated to give a colourless solid. This solid was recrystallized from acetonitrile to give 0.50 g (67%) of 5-carboxy2,3,5,6,7,8-hexahydro-1,3-dioxo-1H-1,2,4-triazolo[1,2-a]pyridazine-2-acetic acid of melting point 224°-226° C. (from acetonitrile).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customto give a colourless solid
  4. customThis solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-8922cc55752e4b18828b08e029f843f3
Source dataset
uspto-grants-1981_12
Patent number
US04307094

Reaction notes

Loading…