Nitric Acid → HCID 178526860, compound

HRID 2409096Notes

Reaction equation

HRID 2409096 reaction equation
[CH:1]1([C:4]2[CH:8]=[CH:7][NH:6][N:5]=2)[CH2:3][CH2:2]1.[N+:9]([O-])([OH:11])=[O:10]>OS(O)(=O)=O>[CH:1]1([C:4]2[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][NH:6][N:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178419915HCID 178419915, compound

Product 1

HCID 178526860HCID 178526860, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a cooling (0° C.) solution of 3-cyclopropyl-1H-pyrazole (1.5 g, 13.89 mmol) in concentrated H2SO4 (20 mL, 98%) was added concentrated HNO3 (20 mL, 65%) over 2 min. The reaction mixture was stirred over 1 hr at this temperature. It was then diluted with ice-water and extracted with EA (30 mL×4). The organic phase was combined and washed with saturated sodium bicarbonate (50 mL). It was dried over Na2SO4 and concentrated in vacuo to give a crude product (1.5 g, 70%). This crude product was pure enough to be delivered or used to the next step reaction. MS: [M+H]+154. 1H NMR (500 MHz, CDCl3) δ 0.97 (m, 2H), 1.22 (m, 2H), 2.66 (m, 1H), 8.20 (s, 1H), 8.38 (s, 1H).

Workup

  1. extractionextracted with EA (30 mL×4)
  2. washwashed with saturated sodium bicarbonate (50 mL)
  3. dry with materialIt was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c3011a518ff449e298b997324ce993c1
Source dataset
uspto-grants-2014_08
Patent number
US08815882B2

Reaction notes

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