Ethanolamine → HCID 178429348, compound

HRID 987607Notes

Reaction equation

HRID 987607 reaction equation
[C:1]([CH2:3][C:4]([O:6]CC)=O)#[N:2].[CH2:9]([CH2:11][NH2:12])[OH:10].[C:13](OCC)(=[O:18])[CH2:14][C:15]([CH3:17])=O>O>[C:1]([C:3]1[C:4](=[O:6])[N:12]([CH2:11][CH2:9][OH:10])[C:13]([OH:18])=[CH:14][C:15]=1[CH3:17])#[N:2]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 7764Ethyl cyanoacetateHCID 8868Ethyl Acetoacetate

Product 1

HCID 178429348HCID 178429348, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

Step 1) Ethyl cyanoacetate (56.5 parts) was added dropwise over 0.25 hours to a stirred solution of ethanolamine (76.25 parts) in water (18 parts) while maintaining the temperature at less than 30° C. Ethyl acetoacetate (65 parts) was then added while maintaining the temperature at less than 30° C. The mixture was stirred at 90° C. for 20 hours, cooled and poured into water (500 parts), the product isolated by filtration, washed with water and dried to give 3-cyano-6-hydroxy4-methyl-1-(2-hydroxyethyl)pyrid-2-one (45 parts).

Workup

  1. temperaturewhile maintaining the temperature at less than 30° C
  2. temperaturewhile maintaining the temperature at less than 30° C
  3. temperaturecooled
  4. customthe product isolated by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-3ce3db5ebf54498494611711b83b0d31
Source dataset
uspto-grants-2003_10
Patent number
US06632858B1

Reaction notes

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