Nitric Acid → HCID 22277496, compound

HRID 1063796Notes

Reaction equation

HRID 1063796 reaction equation
[CH2:1]([C:5]1[NH:9][N:8]=[C:7]([C:10]([OH:12])=[O:11])[CH:6]=1)[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)O.[N+:18]([O-])([OH:20])=[O:19]>>[CH2:1]([C:5]1[NH:9][N:8]=[C:7]([C:10]([OH:12])=[O:11])[C:6]=1[N+:18]([O-:20])=[O:19])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 64851815-Butyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 22277496HCID 22277496, compoundYield 76.7%

Conditions

Temperature
60 °C

Procedure

5-Butyl-1H-pyrazol-3-carboxylic acid (22.6 g, 134 mmol) was added portionwise to concentrated sulfuric acid (100 ml) at room temperature with stirring. The reaction mixture was then heated to 60° C. and concentrated nitric acid (70%, 23.7 ml, 376 mmol) was added dropwise, keeping the temperature at 60° C. The reaction was then stirred at 60° C. for 3 hours, cooled to room temperature and poured onto 50 ml of ice with stirring. After 15 minutes the pale yellow precipitate was isolated by filtration, washed with water and dried under reduced pressure to give 5-butyl-4-nitro-1H-pyrazol-3-carboxylic acid (21.9 g) as a pale yellow solid. 1H NMR (400 MHz, DMSO-D6): δ=2.83-2.92 (2H, t), 1.56-1.64 (2H, quin), 1.22-1.36 (2H, sext), 0.84-0.90 (3H, t) ppm. LRMS (electrospray): m/z [M−H]+ 212. Anal. Found C, 30.19; H, 5.41; N, 13.12. C8H11N3O4. 6 mol H2O requires C, 29.91; H, 7.22; N, 13.08%.

Workup

  1. customat 60° C
  2. stirringThe reaction was then stirred at 60° C. for 3 hours
  3. temperaturecooled to room temperature
  4. stirringwith stirring
  5. customAfter 15 minutes the pale yellow precipitate was isolated by filtration
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-fd13258bd8494e5ebadcfc262bd9b064
Source dataset
uspto-grants-2005_11
Patent number
US06967204B2

Reaction notes

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