HCID 70205854, compound → HCID 18975410, compound

HRID 2393393Notes

Reaction equation

HRID 2393393 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[CH:7]=[C:8]1[C:20]2[N:19]3[CH:21]=[CH:22][N:23]=[C:18]3[C:17](=[O:24])[NH:16][C:15]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2)([O-])=O>CN(C)C=O.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[CH2:7][CH:8]1[C:20]2[N:19]3[CH:21]=[CH:22][N:23]=[C:18]3[C:17](=[O:24])[NH:16][C:15]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2

Participants

4

Reactant 1

HCID 70205854HCID 70205854, compound

Product 1

HCID 18975410HCID 18975410, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

3 g of 10-(3-nitrobenzylidene)-5H-imidazo-(1,2-a]indeno[1,2-e]pyrazin-4-one are hydrogenated at atmospheric pressure and at 50° C. in the presence of 10% palladium-on-charcoal in 100 ml of dimethylformamide. After 20 hours of reaction, the reaction medium is filtered on Celite. The insoluble material is washed with 1 liter of dimethyl sulphoxide and the filtrate is concentrated to dryness under reduced pressure. After drying of the yellow powder thus obtained (5 mmHg; 0.65 kPa) at 65° C., 2.5 g of 10-(3-aminobenzyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one are obtained, the melting point of which is greater than 260° C. (Analysis, C20H16N4O.0.52 H2O.0.30 DMSO; % calculated C: 73.16; H: 4.91; N: 17.06; % found C: 73.2; H: 5.1; N: 17.2).

Workup

  1. customAfter 20 hours of reaction
  2. filtrationthe reaction medium is filtered on Celite
  3. washThe insoluble material is washed with 1 liter of dimethyl sulphoxide
  4. concentrationthe filtrate is concentrated to dryness under reduced pressure
  5. customAfter drying of the yellow powder
  6. customthus obtained (5 mmHg; 0.65 kPa) at 65° C.

Sources & evidence

ORD record
ord-fafe757145b6445d8b52e3fb8deb60ee
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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