Hydrochloric Acid → HCID 67314713, compound

HRID 1011959Notes

Reaction equation

HRID 1011959 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([C:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=O)[C:6](=O)[CH3:7])[CH3:2].Cl.[NH2:19][NH2:20].Cl.C([O-])(O)=O.[Na+]>C(O)C.O.O1CCOCC1>[CH2:1]([O:3][C:4]([C:5]1[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[N:19][NH:20][C:6]=1[CH3:7])=[O:17])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 115031Hydrazinium chlorideHCID 516892Sodium BicarbonateHCID 67314215Ethyl 2-isonicotinoyl-3-oxobutanoate

Product 1

HCID 67314713HCID 67314713, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-oxo-2-(pyridine-4-carbonyl)-butyric acid ethyl ester (1 g, 4.25 mmol) in 10 ml ethanol, were added a solution of hydrazine hydrochloride (291 mg, 4.25 mmol) in 4 ml water and, then 0.1 ml of 4M HCl in dioxane. The yellow solution was stirred 1 h at room temperature, poured on a saturated solution of NaHCO3 and extracted twice with EtOAc. The organic phases were washed with brine, dried over magnesium sulfate, and evaporated to afford the title compound as light yellow solid (815 mg, 83%). MS: 232.1 (MH+).

Workup

  1. extractionextracted twice with EtOAc
  2. washThe organic phases were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-7d36124fae1349858c78fc1f6174af8d
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

Loading…