HCID 56988602, compound → HCID 18975407, compound

HRID 2393372Notes

Reaction equation

HRID 2393372 reaction equation
[C:1]([CH:4]=[C:5]1[C:17]2[N:16]3[CH:18]=[CH:19][N:20]=[C:15]3[C:14](=[O:21])[NH:13][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2)([OH:3])=[O:2]>[OH-].[Na+].O.[Pd]>[C:1]([CH2:4][CH:5]1[C:17]2[N:16]3[CH:18]=[CH:19][N:20]=[C:15]3[C:14](=[O:21])[NH:13][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2)([OH:3])=[O:2]

Participants

5

Reactant 1

HCID 56988602HCID 56988602, compound

Product 1

HCID 18975407HCID 18975407, compoundYield 87.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 19.95 g of 10-(carboxymethyl-ene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one in 720 ml of 1N sodium hydroxide and 200 ml of water is hydrogenated at 1.7 bar and at a temperature in the region of 23° C. for 22 hours in the presence of 2 g of 10% palladium-on-charcoal. The reaction mixture is filtered and the filtrate is acidified with 95 ml of 1N hydrochloric acid. The precipitate formed is filtered off, washed with water (200 ml), then with acetone (5×200 ml) and dried at 80° C. under vacuum (1 mmHg; 0.13 kPa). 17.65 g of 10-(carboxymethyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one are obtained in the form of a light-grey solid, which product is converted into the sodium salt of formula C15H10N3O3Na (Analysis, % calculated C: 59.41, H: 3.32, N: 13.86, O: 15.83, Na: 7.58, % found C: 59.3, H: 2.9, N: 13.7).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water (200 ml)
  5. dry with materialwith acetone (5×200 ml) and dried at 80° C. under vacuum (1 mmHg; 0.13 kPa)

Sources & evidence

ORD record
ord-b043c17bcf8a4f3fa1e02288f7d252a9
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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