Water → Ethyl (pyridin-4-yl)glyoxylate Hydrate

HRID 352822Notes

Reaction equation

HRID 352822 reaction equation
Cl.Br[CH:3]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N-]=[N+]=[N-].[Na+].[OH2:19]>CN(C)C=O>[OH2:5].[N:12]1[CH:13]=[CH:14][C:9]([C:3](=[O:19])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86592085Ethyl 2-bromo-2-(pyridin-4-yl)acetate hydrochloride

Product 1

HCID 86592084Ethyl (pyridin-4-yl)glyoxylate Hydrate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl bromo(pyridin-4-yl)acetate hydrochloride (2.05 g) was dissolved in N,N-dimethylformamide (10 ml) at room temperature, followed by the addition of sodium azide (1.43 g). The resulting mixture was stirred for 30 minutes. After the addition of water and stirring, the insoluble matter was filtered off and the filtrate was concentrated. The residue was extracted with diethyl ether and saturated aqueous NaCl solution. The organic layer thus obtained was dried over anhydrous magnesium sulfate. The filtrate was concentrated and the residue was crystallized from methylene chloride, whereby the title compound (yellow powder, 300 mg) was obtained.

Workup

  1. stirringstirring
  2. filtrationthe insoluble matter was filtered off
  3. concentrationthe filtrate was concentrated
  4. extractionThe residue was extracted with diethyl ether and saturated aqueous NaCl solution
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. concentrationThe filtrate was concentrated
  8. customthe residue was crystallized from methylene chloride, whereby the title compound (yellow powder, 300 mg)
  9. customwas obtained

Sources & evidence

ORD record
ord-af0f406eab674e9abf6da64aae12a3bd
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

Loading…