Nitric Acid → HCID 178526844, compound

HRID 1271120Notes

Reaction equation

HRID 1271120 reaction equation
Cl.[OH:2][C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[N+:9]([O-])([OH:11])=[O:10].O.[OH-].[Na+]>S(=O)(=O)(O)O.C(O)(C)C>[OH:2][C:3]1[N:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 178479648HCID 178479648, compound

Product 1

HCID 178526844HCID 178526844, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 3776IsopropanolSolvent

Procedure

With reference to Scheme 3, to a solution of 2800 g (21.13 mol) of 2-hydroxypyrimidine hydrochloride in 8400 mL of concentrated sulfuric acid was added dropwise 3434 g (52.83 mol) of fuming nitric acid. The solution was heated at reflux for 16 h, then it was allowed to cool to room temperature and was poured slowly into cold water (30 L). The mixture was basified with 50% NaOH to pH 2.5. Isopropyl alcohol (16 L) was added and the mixture was stirred for 60 minutes after which the layers were allowed to separate. The organic layer was diluted with ethyl acetate (16 L) and washed with brine. The organics were concentrated under reduced pressure to yield 2689 g of crude product, which was used in the next step without purification.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 16 h
  3. customto separate
  4. additionThe organic layer was diluted with ethyl acetate (16 L)
  5. washwashed with brine
  6. concentrationThe organics were concentrated under reduced pressure

Sources & evidence

ORD record
ord-69a07d05544b429f8bc90db6e6b5d066
Source dataset
uspto-grants-2007_04
Patent number
US07205307B2

Reaction notes

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