Sulfuric Acid → HCID 53713155, compound

HRID 1492524Notes

Reaction equation

HRID 1492524 reaction equation
C([NH:3][CH:4]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[CH2:5][C:6]1[CH:18]=[CH:17][C:9]([CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=1)=O.S(=O)(=O)(O)O>C(O)C.O1CCCC1.O>[NH2:3][CH:4]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[CH2:5][C:6]1[CH:18]=[CH:17][C:9]([CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=1

Participants

6

Reactant 2

HCID 1118Sulfuric AcidHCID 54406415HCID 54406415, compound

Product 1

HCID 53713155HCID 53713155, compoundYield 95.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Ethyl 4-[2-formamido-2-(3-pyridyl)ethyl]cinnamate (0.40 g) was dissolved in a mixed solvent of 10 ml of ethanol, 10 ml of tetrahydrofuran and 8 ml of water, followed by addition of 0.40 ml of concentrated sulfuric acid and heating to 65 ° C., and stirred for 17 hours. After completion of the reaction, the solvent was evaporated under reduced pressure, followed by addition of CH2Cl2 and water and subsequent gradual addition of saturated aqueous solution of sodium hydrogencarbonate to adjust the mixture to weak alkalinity. The organic phase was separated and extracted from aqueous phase with methanol-methylene chloride (5:95 v/v), followed by washing in saturated aqueous sodium chloride solution, drying over magnesium sulfate and evaporation of the solvent, to produce 0.35 g of ethyl 4-[2-amino-2-(3-pyridyl)ethyl]cinnamate.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. additionfollowed by addition of CH2Cl2 and water and subsequent gradual addition of saturated aqueous solution of sodium hydrogencarbonate
  4. customThe organic phase was separated
  5. extractionextracted from aqueous phase with methanol-methylene chloride (5:95 v/v)
  6. washby washing in saturated aqueous sodium chloride solution
  7. dry with materialdrying over magnesium sulfate and evaporation of the solvent

Sources & evidence

ORD record
ord-b98d240c1fc1437f91d2b65df9dcc4fc
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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