Dimethylamine → HCID 23369747, compound

HRID 1900791Notes

Reaction equation

HRID 1900791 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:13])[NH:7]2.[CH3:14][NH:15][CH3:16].[CH2:17]=O>CN(C)C=O>[CH3:14][N:15]([CH2:17][C:11]1[C:2]([OH:1])=[C:3]2[C:8](=[C:9]([CH3:12])[CH:10]=1)[NH:7][C:6](=[O:13])[CH:5]=[CH:4]2)[CH3:16]

Participants

5

Reactant 3

HCID 674Dimethylamine2×HCID 712Formaldehyde2×HCID 23369598HCID 23369598, compound

Product 1

HCID 23369747HCID 23369747, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5-Hydroxy-8-methylcarbostyril (10.51 g, 60 mmol) and dimethylamine (aqueous 40% solution, 12.07 g, 66 mmol) were dissolved in N,N-dimethylformamide (30 ml). To this solution, formaldehyde (aqueous 37% solution, 5.36 g, 66 mmol) was added slowly at room temperature, and stirred. After 12 hours, dimethylamine (6 g, 33 mmol), formaldehyde (2.79 g, 33 mmol), and N,N-dimethylformamide (20 ml) were added thereto, and the mixture was stirred at room temperature for further 12 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resultant residue was combined with chloroform and n-hexane. Crystals were collected by filtration, and dried under reduced pressure. As a result, 13.23 g of the title compound was obtained as pale reddish gray crystals (95%).

Workup

  1. stirringthe mixture was stirred at room temperature for further 12 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. filtrationCrystals were collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-c7ec74a4c0de4bb29f0e34d12f2853fe
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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