Sodium Hydroxide → HCID 11457847, compound

HRID 2099507Notes

Reaction equation

HRID 2099507 reaction equation
C(O/[CH:4]=[CH:5]/[C:6]([NH:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:7])C.[OH-].[Na+]>>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[N:9]1[CH:4]=[CH:5][C:6](=[O:7])[NH:8]1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 68840644HCID 68840644, compound

Product 1

HCID 11457847HCID 11457847, compound

Procedure

(2E)-3-Ethoxy-N′-pyridin-2-ylprop-2-enohydrazide (8.5 g, 41 mmol) was stirred with concentrated 37% HCl (20 mL) for 3 h. The resulting reaction mixture was adjusted to pH 7 using 1N NaOH (aq) and a precipitate formed. The reaction mixture then extracted with EtOAc (3×50 mL)and washed with brine. The combined organic phase was dried over Na2SO4, concentrated in vacuo purified using liquid chromatography on silica gel eluting with EtOAc (100%) to afford 1-pyridin-2-yl-1,2-dihydro-3H-pyrazol-3-one as a yellow solid. 1H NMR (CD3Cl, 300 MHz) δ 12.00 (br, 1H), 8.43˜8.39 (m, 2H), 7.85 (ddd, 1H), 7.64 (d, 1H), 7.16 (ddd, 1H), 5.99 (d, 1H). MS (ESI) 162 (M++H).

Workup

  1. concentrationwith concentrated 37% HCl (20 mL) for 3 h
  2. customThe resulting reaction mixture
  3. customa precipitate formed
  4. extractionThe reaction mixture then extracted with EtOAc (3×50 mL)
  5. washwashed with brine
  6. dry with materialThe combined organic phase was dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified

Sources & evidence

ORD record
ord-bb0696cb015044d2815c912b2f1f90fa
Source dataset
uspto-grants-2009_08
Patent number
US07569592B2

Reaction notes

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