Sodium Hydroxide → HCID 73864397, compound

HRID 2227499Notes

Reaction equation

HRID 2227499 reaction equation
[C:1]([C:3]([C:18](=[O:27])[NH:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)=[CH:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13]CC)=[O:12])=[CH:7][CH:6]=1)#[N:2].[OH-].[Na+:29]>CO>[C:1]([C:3]([C:18](=[O:27])[NH:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)=[CH:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]([O-:13])=[O:12])=[CH:16][CH:17]=1)#[N:2].[Na+:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 85433124HCID 85433124, compound

Product 1

HCID 73864397HCID 73864397, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl [4-[2-cyano-2-[N-(3-pyridylmethyl)carbamoyl]ethenyl]phenoxy]acetate (730 mg) in 30 ml methanol was stirred with 10 ml of 0.2 mol/l aqueous sodium hydroxide at room temperature for 18 hours. After evaporation of methanol, the reaction mixture was mixed with 100 ml water and then extracted with 30 ml ethyl acetate to remove unreacted components. The aqueous layer was concentrated until a solid came out. A part of the resulting solid was filtered, and then dried over diphosphorus pentaoxide by heating under reduced pressure to give the compound of interest (156 mg, 22%) as a pale yellow solid.

Workup

  1. customAfter evaporation of methanol
  2. additionthe reaction mixture was mixed with 100 ml water
  3. extractionextracted with 30 ml ethyl acetate
  4. customto remove unreacted components
  5. concentrationThe aqueous layer was concentrated until a solid
  6. filtrationA part of the resulting solid was filtered
  7. dry with materialdried over diphosphorus pentaoxide
  8. temperatureby heating under reduced pressure
  9. customto give the compound of interest (156 mg, 22%) as a pale yellow solid

Sources & evidence

ORD record
ord-710c22e17bb84754a53cb81a2eb45ddc
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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