Acetic Acid → HCID 87481606, compound

HRID 2241416Notes

Reaction equation

HRID 2241416 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][NH2:8].[C:9](O)(=[O:11])[CH3:10].C(C=O)=O.C(=O)([O-])O.[Na+]>O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7]/[N:8]=[CH:10]/[CH:9]=[O:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7860GlyoxalHCID 786452-HydrazinopyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 87481606HCID 87481606, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the 1-(pyridin-2-yl)hydrazine (2.00 g, 18.33 mmol), water (13 mL), and acetic acid (10.49 ml, 183.3 mmol) was added with stirring into a 40% aqueous solution of glyoxal (10.51 ml, 91.63 mmol) over 20 minutes. Stirring was continued for 18 hours and then the aqueous was extracted with EtOAc. The diluted aqueous layer was slowly basified with sodium hydrogen carbonate (15.40 g, 183.3 mmol). The resulting solids were collected by filtration and washed with water to afford 1.65 g (85%) of the desired product and dimer. LRMS (apci pos): 150 (M+H).

Workup

  1. additionwas added
  2. extractionthe aqueous was extracted with EtOAc
  3. filtrationThe resulting solids were collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-ebc490b6d8cd4bcdb390d64589ed3d64
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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