Nitric Acid → HCID 178440446, compound

HRID 895822Notes

Reaction equation

HRID 895822 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 suctiod 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 suctiod

Sources & evidence

ORD record
ord-d229b954c4b043f080d1f25fae7bb852
Source dataset
uspto-grants-2005_07
Patent number
US06916927B2

Reaction notes

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