Acetic Acid → HCID 13007948, compound

HRID 497999Notes

Reaction equation

HRID 497999 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:5]=[CH:4][C:3]=1C(OCC)=O.Cl.C(O)(=O)C>[OH-].[Na+]>[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[N:6]1[C:2]([NH2:1])=[CH:3][CH:4]=[N:5]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 742041ethyl 5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate

Product 1

HCID 13007948HCID 13007948, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of ethyl 5-amino-1-(2-pyridinyl)-1H-pyrazole-4-carboxylate (27.9 g, 120 mmol) in 4N sodium hydroxide (300 mL) was heated under reflux for 1 hour. The suspension was allowed to cool to room temperature, neutralized by the addition of conc. hydrochloric acid, and further made acidic by the addition of acetic acid. The resulting crystals were collected by filtration, washed with ethanol, and air dried. The crystals thus obtained were subjected to heat at 200° C., and washed with diethylether to give the title compound (6.02 g, 31% yield). NMR (CDCl3) δ: 5.51 (1H, d, J=1.8 Hz), 5.95 (2H, br s), 7.07-7.13 (1H, m), 7.42 (1H, d, J=1.8 Hz), 7.75-7.84 (1H, m), 7.98 (1H, d, J=8.4 Hz), 8.33 (1H, dd, J=1.6 Hz, 4.6 Hz).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with ethanol, and air
  5. customdried
  6. customThe crystals thus obtained
  7. temperatureto heat at 200° C.
  8. washwashed with diethylether

Sources & evidence

ORD record
ord-17fbd950f2b845b1860385f77a51f22a
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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