Ethyl Acetoacetate → HCID 178429265, compound

HRID 878534Notes

Reaction equation

HRID 878534 reaction equation
[NH:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][N:10]=1)[C:6]#[N:7])[NH2:2].O=[C:12]([CH3:19])[CH2:13][C:14](OCC)=[O:15]>CCO.CC(O)=O>[OH:15][C:14]1[N:1]([C:3]2[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][N:10]=2)[N:2]=[C:12]([CH3:19])[CH:13]=1

Participants

5

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 201187142-Hydrazinylpyridine-4-carbonitrile

Product 1

HCID 178429265HCID 178429265, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-hydrazinylisonicotinonitrile (536 mg, 4 mmol, PREPARATION 2) and ethyl 3-oxobutanoate (780 mg, 6 mmol) in EtOH (10 mL) and AcOH (2 mL) was stirred at 90° C. overnight. The reaction mixture was cooled, concentrated, and purified by flash column chromatography (CH2Cl2) to afford the title compound (500 mg, 67%) as a yellow solid. [M+H] Calc'd for C10H8N4O, 201; Found, 201.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. custompurified by flash column chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-2e3ea189678942768e4f5a7e806c0f46
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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