Methanol → HCID 136344261, compound

HRID 1669380Notes

Reaction equation

HRID 1669380 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[C:11](=[O:23])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([OH:22])=O)[CH:15]=1.ON1[C:29](=[O:30])[CH2:28]CC1=O.C1([N:38]=C=NC2CCCCC2)CCCCC1.CO>CN(C)C=O>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[C:11](=[O:23])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([NH:38][CH2:28][CH2:29][OH:30])=[O:22])[CH:15]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 136344262HCID 136344262, compound

Product 1

HCID 136344261HCID 136344261, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixed solution of 1.57 g of 4-hydroxy-3-[3-(3-carboxyphenyl)-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone, 50 ml of dimethylformamide and 0.58 g of N-hydroxysuccinimide was added a solution of 1.03 g of dicyclohexylcarbodiimide in 5 ml of dimethylformamide, and this was stirred at room temperature overnight. Insolubles were filtered, 0.33 ml of ethanolamine was added to the filtrate, and this was stirred at room temperature for 2.5 hours. To the residue obtained by concentration under reduced pressure was added 30 ml of methanol, and this was heated under reflux. After ice-cooling, crystals were filtered, washed with methanol, and dried to obtain 0.61 g of 4-hydroxy-3-[3-[3-[(2-hydroxyethyl)aminocarbonyl]phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone [Compound No. (96a)] as a yellow crystal.

Workup

  1. filtrationInsolubles were filtered
  2. addition0.33 ml of ethanolamine was added to the filtrate
  3. stirringthis was stirred at room temperature for 2.5 hours
  4. customTo the residue obtained by concentration under reduced pressure
  5. temperaturethis was heated
  6. temperatureunder reflux
  7. temperatureAfter ice-cooling
  8. filtrationcrystals were filtered
  9. washwashed with methanol
  10. customdried

Sources & evidence

ORD record
ord-69b7ccf15f3540deb95279718546d260
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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