Sodium Hydroxide → HCID 57285833, compound

HRID 2393364Notes

Reaction equation

HRID 2393364 reaction equation
C(C1C=CC=CC=1[CH:6]=[C:7]1[C:19]2[N:18]3[CH:20]=[CH:21][N:22]=[C:17]3[C:16](=[O:23])[NH:15][C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2)(O)=O.C1N2C3CC4C=CC=CC=4C=3NC(=O)C2=NC=1.C[O:46][C:47]([C:49]1[CH:50]=[C:51]([CH:54]=[CH:55][CH:56]=1)C=O)=[O:48].[H-].[Na+].[OH-].[Na+]>O.C(O)(=O)C.CS(C)=O>[C:47]([C:49]1[CH:56]=[C:55]([CH:54]=[CH:51][CH:50]=1)[CH:6]=[C:7]1[C:19]2[N:18]3[CH:20]=[CH:21][N:22]=[C:17]3[C:16](=[O:23])[NH:15][C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2)([OH:48])=[O:46]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 639145Methyl 3-formylbenzoateHCID 103535495H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-oneHCID 70205095HCID 70205095, compound

Product 1

HCID 57285833HCID 57285833, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

The process is performed as in Example 3 for the preparation of 10-(2-carboxybenzylidene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one but starting with 5 g of 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 100 ml of dimethyl sulphoxide, 4.04 g of 3-methoxycarbonylbenzaldehyde and 1.6 g of 80% sodium hydride. After treatment of the reaction mixture with 100 ml of water and 10 ml of acetic acid, the suspension obtained is filtered; the insoluble product is washed with water, air-dried and then triturated with 80 ml of dimethylformamide, filtered off and dried. The yellow solid obtained (1 g) is suspended in 100 ml of water and, after addition of 25 ml of 0.1N sodium hydroxide, the solution is filtered and acidified with 2.5 ml of 1N hydrochloric acid. The precipitate formed is washed with water, triturated with 50 ml of methanol and dried at 60° C. under vacuum (1 mmHg; 0.13 kPa). 0.8 g of 10-(3-carboxybenzylidene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is obtained in the form of a yellow solid melting above 260° C., which product is converted into the disodium salt of formula C21 H11N3O3Na2 (Analysis, % calculated C 63.17, H: 2.78, N: 10.52, O: 12.02, Na : 11.51, % found C: 62.9, H: 2.6, N: 10.2).

Workup

  1. filtrationis filtered
  2. washthe insoluble product is washed with water
  3. customair-dried
  4. customtriturated with 80 ml of dimethylformamide
  5. filtrationfiltered off
  6. customdried
  7. customThe yellow solid obtained (1 g)
  8. filtrationthe solution is filtered
  9. customThe precipitate formed
  10. washis washed with water
  11. customtriturated with 50 ml of methanol
  12. customdried at 60° C. under vacuum (1 mmHg; 0.13 kPa)

Sources & evidence

ORD record
ord-65b4c3599b074314964e3ff0994610b6
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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