Methane → HCID 13151641, compound

HRID 2290252Notes

Reaction equation

HRID 2290252 reaction equation
C([N:8]1[C:16]2[N:15]=[CH:14][N:13]([CH2:17][CH3:18])[C:12]=2[C:11](=[O:19])[N:10]([CH2:20][CH3:21])[C:9]1=[O:22])C1C=CC=CC=1.C>C(O)(=O)C.[Pd]>[CH2:20]([N:10]1[C:11](=[O:19])[C:12]2[N:13]([CH2:17][CH3:18])[CH:14]=[N:15][C:16]=2[NH:8][C:9]1=[O:22])[CH3:21]

Participants

5

Reactant 2

HCID 297MethaneHCID 20157768HCID 20157768, compound

Product 1

HCID 13151641HCID 13151641, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

18 g of 3-benzyl-1,7-diethylxanthine (melting point 119° C.) in 1,500 ml of glacial acetic acid were hydrogenated in the presence of 2.5 g of 10% palladium on active charcoal at 80° C. and under 3.4 bar while shaking for 47 hours. After cooling down, the mixture was covered with an atmosphere of nitrogen while the catalyst was filtered off and the filtrate was evaporated under reduced pressure. The residue was dissolved in a mixture of 250 ml of methylene chloride and 100 ml of 1N sodium hydroxide solution. After washing the methylene chloride phase again with 1N sodium hydroxide solution, the combined aqueous phases were adjusted to pH 6 by adding 33% strength sulfuric acid dropwise with stirring. After washing to neutrality and drying the precipitate produced, 8.1 g (64.5% of theory) of 1,7-diethylxanthine, of melting point 204°-205° C., were obtained.

Workup

  1. temperatureAfter cooling down
  2. filtrationwas filtered off
  3. customthe filtrate was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in a mixture of 250 ml of methylene chloride and 100 ml of 1N sodium hydroxide solution
  5. washAfter washing the methylene chloride phase again with 1N sodium hydroxide solution
  6. additionby adding 33% strength sulfuric acid dropwise
  7. stirringwith stirring
  8. washAfter washing to neutrality
  9. customdrying the precipitate
  10. customproduced

Sources & evidence

ORD record
ord-49e3c8f179414fb6a0cd374f76f57f6f
Source dataset
uspto-grants-1986_10
Patent number
US04616020

Reaction notes

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