Xanthine → Hypoxanthine

HRID 2227361Notes

Reaction equation

HRID 2227361 reaction equation
[NH:1]1[C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[NH:4][C:2]1=O>C(O)CC.[Ni]>[NH:1]1[C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]=[CH:2]1

Participants

4

Reactant 1

HCID 1188Xanthine

Product 1

HCID 135398638HypoxanthineYield 61.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 10311-PropanolSolvent

Procedure

A solution with 2.34 g (4.25 mM) of the above xanthine (B.) and 2.5 g of Raney-nickel (treated with 0.1% of aqueous acetic acid) were refluxed in 35 ml of 1-propanol. After 2.5 hr the nickel was filtered off and the solvent evaporated in vacuo. The residue was dissolved in ethyl acetate, extracted with sodium bicarbonate solution and concentrated in vacuo to about 10 ml. Over night crystallization gave 1.29 g (58.6%) of hypoxanthine with mp 156-157° C.

Workup

  1. filtrationAfter 2.5 hr the nickel was filtered off
  2. customthe solvent evaporated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. extractionextracted with sodium bicarbonate solution
  5. concentrationconcentrated in vacuo to about 10 ml
  6. customOver night crystallization

Sources & evidence

ORD record
ord-1f46db88c5e8437ab3e8a73f210475dd
Source dataset
uspto-grants-2002_07
Patent number
US06413975B1

Reaction notes

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