Ammonium formate → HCID 54406415, compound

HRID 1492523Notes

Reaction equation

HRID 1492523 reaction equation
O=[C:2]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[CH2:3][C:4]1[CH:16]=[CH:15][C:7]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1.[CH:23]([O-:25])=O.[NH4+:26]>O>[CH:23]([NH:26][CH:2]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[CH2:3][C:4]1[CH:16]=[CH:15][C:7]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)=[O:25]

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 54503053HCID 54503053, compound

Product 1

HCID 54406415HCID 54406415, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 4-[2-oxo-2-(3-pyridyl)ethyl]cinnamate (1.0 g) and ammonium formate (4.28 g) were stirred at 140° C. for four hours. To the reaction mixture was added water, followed by extraction with methylene chloride and washing of the organic phase in saturated aqueous sodium chloride solution, and dried over magnesium sulfate. Then, the solvent was evaporated off under reduced pressure. The residue obtained was subjected to chromatography on a silica gel column, to yield 0.72 g of ethyl 4-[2-formamido-2-(3-pyridyl)ethyl]cinnamate from a fraction eluted with methanolmethylene chloride (4:96 v/v).

Workup

  1. extractionfollowed by extraction with methylene chloride
  2. washwashing of the organic phase in saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThen, the solvent was evaporated off under reduced pressure
  5. customThe residue obtained

Sources & evidence

ORD record
ord-af7d849508bb4521bc722a05c9ac5a05
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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