Sodium hydride → HCID 136344251, compound

HRID 1669374Notes

Reaction equation

HRID 1669374 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:21])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=1.[H-].[Na+].Cl.Cl[CH2:26][CH2:27][N:28]([CH3:30])[CH3:29]>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:21])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 136344249HCID 136344249, compound

Product 1

HCID 136344251HCID 136344251, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.58 g of 4-hydroxy-3-[3-(3-hydroxyphenyl)-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone in 10 ml of dimethylformamide was added 0.32 g of sodium hydride (60% oily), and this was stirred at room temperature for 1 hour. To the reaction mixture was added 0.25 g of 2-chloroethyldimethylamine hydrochloride, and this was heated at 60° C. for 4 hours. The solvent was distilled off under reduced pressure, and the precipitated crystals were filtered, washed with t-butyl methyl ether, and dried to obtain 0.21 g of 4-hydroxy-3-[3-[3-(2-dimethylaminoethoxy)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone [Compound No. (56a)] as a yellow crystal.

Workup

  1. temperaturethis was heated at 60° C. for 4 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with t-butyl methyl ether
  5. customdried

Sources & evidence

ORD record
ord-ca8585b5c0504649a051664e4cc42e7b
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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