Nitric Acid → HCID 178440446, compound

HRID 2229793Notes

Reaction equation

HRID 2229793 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[CH2:10]([C:13]1[CH:17]=[C:16]([C:18]([OH:20])=[O:19])[NH:15][N:14]=1)[CH2:11][CH3:12]>>[N+:6]([C:17]1[C:13]([CH2:10][CH2:11][CH3:12])=[N:14][NH:15][C:16]=1[C:18]([OH:20])=[O:19])([O-:9])=[O:7]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 178439322HCID 178439322, compound

Product 1

HCID 178440446HCID 178440446, compound

Conditions

Temperature
50 °C

Procedure

Fuming sulphuric acid (17.8 ml) was added dropwise to stirred, ice-cooled fuming nitric acid (16.0 ml), the resulting solution heated to 50° C., then 3-n-propyl-1H-pyrazole-5-carboxylic acid (Chem. Pharm. Bull., 1984, 32, 1568; 16.4 g, 0.106 mol) added portionwise over 30 minutes whilst maintaining the reaction temperature below 60° C. The resulting solution was heated for 18 hours at 60° C., allowed to cool, then poured onto ice. The white precipitate was collected, washed with water and dried by suction to yield the title compound (15.4 g), m.p. 170-172° C. Found: C, 42.35; H, 4.56; N, 21.07. C7H9N3O4 requires C, 42.21; H, 4.55; N, 21.10%. δ (DMSOd6): 0.90 (3H,t), 1.64 (2H,m), 2.83 (2H,m), 14.00 (1H,s).

Workup

  1. temperaturewhilst maintaining the reaction temperature below 60° C
  2. temperatureThe resulting solution was heated for 18 hours at 60° C.
  3. temperatureto cool
  4. additionpoured onto ice
  5. customThe white precipitate was collected
  6. washwashed with water
  7. customdried by suction

Sources & evidence

ORD record
ord-f564c459099f46fe9260f985dc098c88
Source dataset
uspto-grants-2002_07
Patent number
US06420557B1

Reaction notes

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