Ethanol → HCID 178470503, compound

HRID 872919Notes

Reaction equation

HRID 872919 reaction equation
CCOC([CH2:6][CH2:7][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=O)=O.Cl.Cl.[NH2:17][NH2:18].[OH2:19].[C:20]([O-])(O)=O.[Na+].[CH2:25](O)[CH3:26]>>[CH2:25]([O:19][C:20]1[NH:18][N:17]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:7]=1[CH3:6])[CH3:26]

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 17548Hydrazine, dihydrochlorideHCID 80070Diethyl alpha-ketoglutarateHCID 516892Sodium Bicarbonate

Product 1

HCID 178470503HCID 178470503, compoundYield 80%

Procedure

A solution of diethyl oxalpropionate (9.15 ml, 49.5 mmol) and hydrazine dihydrochloride (6.23 g, 59.3 mmol) in ethanol (50 ml) was refluxed for 1 h. The mixture was then cooled and water (150 ml) was added. The solution was neutralised with solid NaHCO3 and extracted four times with EtOAc. The organic phase was washed with brine and water, dried with Na2SO4 and evaporated to dryness affording 7.81 g (80%) of the title compound. LC-MS: [M+1]=199.22.

Workup

  1. temperatureThe mixture was then cooled
  2. extractionextracted four times with EtOAc
  3. washThe organic phase was washed with brine and water
  4. dry with materialdried with Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-ff515dbe94454f91bfb10d0602cd17dc
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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