2-Hydrazinopyridine → HCID 58840936, compound

HRID 1993937Notes

Reaction equation

HRID 1993937 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][NH2:8].C[O:10][C:11](=O)[C:12]#[C:13][CH3:14].CC(C)([O-])C.[K+]>C(O)(C)(C)C.O>[CH3:14][C:13]1[N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[NH:8][C:11](=[O:10])[CH:12]=1

Participants

6

Reactant 3

HCID 786452-HydrazinopyridineHCID 141019Methyl but-2-ynoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 58840936HCID 58840936, compoundYield 18.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent2×

Procedure

To a solution of pyridin-2-yl-hydrazine (1 g) in tert-butanol (15 mL) at 30° C. was added but-2-ynoic acid methyl ester (1 g). The reaction vessel was then cooled in an ice bath was treated with potassium tert butoxide (2 g) portionwise. The resulting suspension was stirred at ambient temperature for 16 hours. The tert-butanol was reduced in vacuo and the residue was taken up in water. The aqueous layer was extracted once with DCM. The aqueous layer was then acidified with AcOH to pH=3 and the resulting precipitate was collected by filtration and washed with water. The solid was collected and dried over P2O5 in a dessicator to give 5-methyl-1-pyridin-2-yl-1,2-dihydro-pyrazol-3-one (0.3 g) as a white solid. MS (ESI+): 176.3 [M+H]+).

Workup

  1. temperatureThe reaction vessel was then cooled in an ice bath
  2. extractionThe aqueous layer was extracted once with DCM
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customThe solid was collected
  6. dry with materialdried over P2O5 in a dessicator

Sources & evidence

ORD record
ord-bdaf23f6363d4e4c9c789c2b2bd8fd40
Source dataset
uspto-grants-2010_01
Patent number
US07652057B2

Reaction notes

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