Nitric Acid → HCID 22277469, compound

HRID 1063811Notes

Reaction equation

HRID 1063811 reaction equation
[CH:1]1([C:6]2[NH:10][N:9]=[C:8]([C:11]([OH:13])=[O:12])[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)(O)O.[N+:19]([O-])([OH:21])=[O:20]>>[CH:1]1([C:6]2[NH:10][N:9]=[C:8]([C:11]([OH:13])=[O:12])[C:7]=2[N+:19]([O-:21])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 4542029HCID 4542029, compound

Product 1

HCID 22277469HCID 22277469, compoundYield 43.7%

Conditions

Temperature
60 °C

Procedure

5-Cyclopentyl-1H-pyrazol-3-carboxylic acid (13 g, 72.1 mmol) was added portionwise to concentrated sulfuric acid (75 ml) at room temperature with stirring. The reaction mixture was then heated to 60° C. and concentrated nitric acid (70%, 12.7 ml, 202 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 precipitate was isolated by filtration, washed with water and dried under reduced pressure to give 5-cyclopentyl-4-nitro-1H-pyrazol-3-carboxylic acid (7.1 g) as a yellow solid. 1H NMR (400 MHz, DMSO-D6): δ=14.00-14.41 (1H, brs), 13.28-13.85 (1H, brs), 3.20-3.56 (1H, brs, partially masked by solvent), 1.96-2.10 (2H, m), 1.54-1.80 (6H, 2×m) ppm. LRMS (electrospray): m/z [M−H]+ 224, [2M−H]+ 449. Anal. Found C, 43.83; H, 5.35; N, 16.94. C9H11N3O4. 1.2 mol H2O requires C, 43.80; H, 5.47; N, 17.02%.

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 precipitate was isolated by filtration
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-d80bca59de08492aa94745b93717d431
Source dataset
uspto-grants-2005_11
Patent number
US06967204B2

Reaction notes

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