Hydrochloric Acid → 8-chloro-3-methyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione

HRID 1791992Notes

Reaction equation

HRID 1791992 reaction equation
[N+]([O-])(O)=O.[CH3:5][N:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[C:9](=[O:15])[NH:8][C:7]1=[O:16].[ClH:17]>C(O)(=O)C>[Cl:17][C:12]1[NH:11][C:10]2[C:9](=[O:15])[NH:8][C:7](=[O:16])[N:6]([CH3:5])[C:14]=2[N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 706393-Methylxanthine

Product 1

HCID 126175848-chloro-3-methyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Nitric acid (9 ml) was slowly added dropwise to a suspension of 3-methylxanthine (10 g) in acetic acid (180 ml) at 100° C., and the resulting white suspension was stirred at 100° C. for 30 minutes followed by 140° C. for 20 minutes. After cooling the reaction solution to room temperature, the solvent was removed by distillation at reduced pressure at 60° C. to give a yellow solid. The resulting yellow solid was washed with water, and recrystallization from 0.5 M hydrochloric acid gave a pale yellow solid. A suspension of the solid in concentrated hydrochloric acid (500 ml) was stirred at 110° C. for 15 minutes, then the reaction solution was cooled to room temperature, and the solvent was removed by distillation at reduced pressure to give a yellow-white solid. Recrystallization of the resulting solid from water gave 6.75 g of the title compound.

Workup

  1. waitfollowed by 140° C. for 20 minutes
  2. temperatureAfter cooling the reaction solution to room temperature
  3. customthe solvent was removed by distillation at reduced pressure at 60° C.
  4. customto give a yellow solid
  5. washThe resulting yellow solid was washed with water, and recrystallization from 0.5 M hydrochloric acid
  6. customgave a pale yellow solid
  7. stirringwas stirred at 110° C. for 15 minutes
  8. temperaturethe reaction solution was cooled to room temperature
  9. customthe solvent was removed by distillation at reduced pressure
  10. customto give a yellow-white solid
  11. customRecrystallization of the resulting solid from water

Sources & evidence

ORD record
ord-7a685cf4acb941ba9742393b1ac2b3b1
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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