Sodium Bicarbonate → HCID 18950739, compound

HRID 1492558Notes

Reaction equation

HRID 1492558 reaction equation
O=[C:2]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH2:3][CH2:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=1.[CH:24]([O-:26])=O.[NH4+:27].C(=O)([O-])O.[Na+]>>[CH:24]([NH:27][CH:2]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH2:3][CH2:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=1)=[O:26]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723923Ammonium formateHCID 18950751HCID 18950751, compound

Product 1

HCID 18950739HCID 18950739, compoundYield 44.6%

Procedure

1.95 g of ethyl 4-[3-oxo-3-(3-pyridyl)propyl]phenoxyacetate and 5.00 g of ammonium formate were stirred at 165° C. for 1.5 hours. To the reaction mixture was added aqueous sodium hydrogencarbonate solution, which was then extracted with ethyl acetate, and the organic phases combined were washed in saturated aqueous sodium chloride, dried over magnesium sulfate, and the solvent was then distilled off. The obtained residue was subjected to chromatography on a silica gel column, and from a fraction eluted with methanol-methylene chloride (5:95 v/v) was obtained 0.95 g of ethyl 4-[3-formamido-3-(3-pyridyl)propyl]phenoxyacetate.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washthe organic phases combined were washed in saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was then distilled off
  5. washfrom a fraction eluted with methanol-methylene chloride (5:95 v/v)

Sources & evidence

ORD record
ord-45926debfc114aad9e2bf1f6bc11cb82
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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