Nitric Acid → 6-Methyl-5-nitrouracil

HRID 964706

Reaction equation

HRID 964706 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[NH:5][C:4](=[O:9])[CH:3]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[N+:24]([O-])([OH:26])=[O:25]>>[N+:24]([C:3]1[C:4](=[O:9])[NH:5][C:6](=[O:8])[NH:7][C:2]=1[CH3:1])([O-:26])=[O:25]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 122836-MethyluracilHCID 14812Phosphorus oxide (P4O10)

Product 1

HCID 855236-Methyl-5-nitrouracilYield 54%

Procedure

50.5 g (0.40 mol) of 6-methyluracil (Merck) are introduced in portions over the course of one hour with stirring at 02 to +5° C. into a solution of 200 ml of 100% nitric acid (fuming) and 50 g of phosphorus pentoxide. When the exothermic reaction is complete, the mixture is stirred at +5° C. for a further 5 hours. The reaction mixture is subsequently poured into 1 kg of ice-water. The resultant precipitate is filtered, washed with water and then dried to constant weight, giving 37 g (54%) of 5-nitro-6-methyluracil, pale-yellow powder, m.p. 281° C. with decomposition.

Workup

  1. customWhen the exothermic reaction
  2. filtrationThe resultant precipitate is filtered
  3. washwashed with water
  4. customdried to constant weight

Sources & evidence

ORD record
ord-fe17544ea42c44e39fef7b3e22a9b8bd
Source dataset
uspto-grants-1998_06
Patent number
US05770643

Linked notes

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