Nitric Acid → 1,3-Di-n-butyl-8-nitro Xanthine

HRID 3628

Reaction equation

HRID 3628 reaction equation
[CH2:1]([N:5]1[C:14](=[O:15])[C:13]2[NH:12][CH:11]=[N:10][C:9]=2[N:8]([CH2:16][CH2:17][CH2:18][CH3:19])[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4].[N+:20]([O-])([OH:22])=[O:21]>C(O)(=O)C>[CH2:1]([N:5]1[C:14](=[O:15])[C:13]2[NH:12][C:11]([N+:20]([O-:22])=[O:21])=[N:10][C:9]=2[N:8]([CH2:16][CH2:17][CH2:18][CH3:19])[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1014211,3-Dibutylxanthine

Product 1

HCID 99444751,3-Di-n-butyl-8-nitro Xanthine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
5 °C

Procedure

1,3-Di-n-butylxanthine (73 g, 0.28 mol) was dissolved in acetic acid (120 ml) and then treated with concentrated nitric acid (49 g) at 87° C. After 1 hour, the mixture was cooled to 5° C., the resulting yellow precipitate filtered off and washed with water (50 ml). The yellow crystals were dissolved in dichloromethane and washed twice with water. The separated organic layer was then dried (anhydrous sodium sulphate) and concentrated to give a crystalline product, yield 73 g (86%), m.pt 168° C.

Workup

  1. filtrationthe resulting yellow precipitate filtered off
  2. washwashed with water (50 ml)
  3. dissolutionThe yellow crystals were dissolved in dichloromethane
  4. washwashed twice with water
  5. dry with materialThe separated organic layer was then dried (anhydrous sodium sulphate)
  6. concentrationconcentrated
  7. customto give a crystalline product, yield 73 g (86%), m.pt 168° C.

Sources & evidence

ORD record
ord-cc12e5c031414063a4d8c42a97e5d896
Source dataset
uspto-grants-1998_03
Patent number
US05734051

Linked notes

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