Water → HCID 18918193, compound

HRID 1290775Notes

Reaction equation

HRID 1290775 reaction equation
[CH:1](=[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]=[C:12]([Cl:25])[CH:11]=[CH:10][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H].O>CO.CN(C)C=O.[Pd]>[CH2:1]([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]=[C:12]([Cl:25])[CH:11]=[CH:10][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 962WaterHCID 70344553HCID 70344553, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18918193HCID 18918193, compoundYield 28.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

2.1 g of 10-benzylidene-7-chloro-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one dissolved in 20 ml of a mixture of methanol and dimethylformamide (1/1 by volume) are hydrogenated at a temperature in the region of 20° C. and at a pressure of 9.6 bar of hydrogen for 24 hours in the presence of 10% palladium on charcoal. The catalyst is then filtered off under inert atmosphere and the solvents are evaporated off. The brown oil obtained is taken up in 25 ml of methanol and, after addition of 50 ml of distilled water, a pink precipitate forms. The solid thus obtained (1.3 g) is recrystallized in 150 ml of a mixture of methanol and water (1/2 by volume). 0.6 g of 10-benzyl-7-chloro-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is obtained, in the form of a beige solid the melting point of which is greater than 260° C. (Analysis C20H14ClN3 O·0.41 H2O % calculated C: 69.07; H: 4.06; Cl: 10.19; N: 12.08; % found C: 69.0; H: 3.9; Cl: 10.5; N: 12.4).

Workup

  1. filtrationThe catalyst is then filtered off under inert atmosphere
  2. customthe solvents are evaporated off
  3. customThe brown oil obtained
  4. customThe solid thus obtained (1.3 g)
  5. customis recrystallized in 150 ml of a mixture of methanol and water (1/2 by volume)

Sources & evidence

ORD record
ord-c31010139c214e69b061ae89ee037270
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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