Nitric Acid → 1,3-Dicyclopropylmethyl-8-nitro xanthine

HRID 1860965Notes

Reaction equation

HRID 1860965 reaction equation
[CH:1]1([CH2:4][N:5]2[C:14](=[O:15])[C:13]3[NH:12][CH:11]=[N:10][C:9]=3[N:8]([CH2:16][CH:17]3[CH2:19][CH2:18]3)[C:6]2=[O:7])[CH2:3][CH2:2]1.[N+:20]([O-])([OH:22])=[O:21]>C(O)(=O)C>[CH:1]1([CH2:4][N:5]2[C:14](=[O:15])[C:13]3[NH:12][C:11]([N+:20]([O-:22])=[O:21])=[N:10][C:9]=3[N:8]([CH2:16][CH:17]3[CH2:19][CH2:18]3)[C:6]2=[O:7])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 152913031,3-Dicyclopropylmethyl xanthine

Product 1

HCID 98576581,3-Dicyclopropylmethyl-8-nitro xanthineYield 56.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
5 °C

Procedure

1,3-Di-cyclopropylmethyl xanthine (20 g, 0.76 mol) was dissolved in acetic acid (33 ml) and then treated with concentrated nitric acid (13.2 g). at 87° C. After 1 hour, the mixture was cooled to 5° C. and the resulting yellow precipitate filtered off. The yellow crystals were dissolved in dichloromethane and washed with water. The separated organic layer was then dried over anhydrous sodium sulphate and concentrated in vacuo. The product crystallized from the concentrate to yield a yellow crystalline product yield 12.2 g, (56.5%), m.pt. 207° C. (with decomposition).

Workup

  1. customat 87° C
  2. filtrationthe resulting yellow precipitate filtered off
  3. dissolutionThe yellow crystals were dissolved in dichloromethane
  4. washwashed with water
  5. dry with materialThe separated organic layer was then dried over anhydrous sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe product crystallized from the
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-06b64c1c1ec84ee997f04b98d32c5250
Source dataset
uspto-grants-2003_03
Patent number
US06531600B1

Reaction notes

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