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

HRID 1602137Notes

Reaction equation

HRID 1602137 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-bb30ceba81694823919a5a010f609538
Source dataset
uspto-grants-1999_11
Patent number
US05981535

Reaction notes

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