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

HRID 568132

Reaction equation

HRID 568132 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, 0.076 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. filtrationthe resulting yellow precipitate filtered off
  2. dissolutionThe yellow crystals were dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialThe separated organic layer was then dried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe product crystallized from the
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-5a7df32243544a3395d9d31276fc7959
Source dataset
uspto-grants-2001_01
Patent number
US06180791B2

Linked notes

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