Ethyl 2-methylacetoacetate → HCID 178433908, compound

HRID 514326

Reaction equation

HRID 514326 reaction equation
[NH:1]([C:3]1[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][N:4]=1)[NH2:2].C([O:13][C:14](=O)[CH:15]([CH3:19])[C:16](=O)[CH3:17])C>CCO.CC(O)=O>[OH:13][C:14]1[N:1]([C:3]2[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][N:4]=2)[N:2]=[C:16]([CH3:17])[C:15]=1[CH3:19]

Participants

5

Reactant 2

HCID 701Ethyl 2-methylacetoacetateHCID 201187142-Hydrazinylpyridine-4-carbonitrile

Product 1

HCID 178433908HCID 178433908, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-hydrazinylpyridine-4-carbonitrile (134 mg, 1 mmol, PREPARATION 2) and 2-methyl-3-oxo-butyric acid ethyl ester (158 mg, 1.1 mmol) in EtOH (5 mL) and AcOH (1 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 (100 mg, 47%) as an orange solid. [M+H] Calc'd for C11H10N4O, 215. Found, 215.

Workup

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

Sources & evidence

ORD record
ord-1bc84d3b06184c8582c335a76ca23ee2
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Linked notes

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