Dimethylformamide → HCID 14986995, compound

HRID 727786Notes

Reaction equation

HRID 727786 reaction equation
CN(C)C=O.[OH:6][C:7]1[CH:28]=[CH:27][C:10]2[CH2:11][CH2:12][CH:13]3[C:18]([C:9]=2[CH:8]=1)=[N:17][N:16]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[C:15](=[O:26])[CH2:14]3.[H-].[Na+].[CH3:31][N:32]([CH3:37])[CH2:33][CH2:34][CH2:35]Cl>O>[CH3:31][N:32]([CH3:37])[CH2:33][CH2:34][CH2:35][O:6][C:7]1[CH:28]=[CH:27][C:10]2[CH2:11][CH2:12][CH:13]3[C:18]([C:9]=2[CH:8]=1)=[N:17][N:16]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[C:15](=[O:26])[CH2:14]3

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 14986984HCID 14986984, compound

Product 1

HCID 14986995HCID 14986995, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 60 ml of dry dimethylformamide is added 6.1 g of 9-hydroxy-2-(4-methylphenyl)-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one, and 0.96 g of 60% sodium hydride is added thereto while stirring at room temperature. After stirring at room temperature for 1 hour, 2.8 g of 3-dimethylaminopropyl chloride is added to the mixture. After the mixture is stirred over water bath under heating at 40°-50° C. for 5 hours, the reaction mixture is poured into a large amount of water, followed by extraction with chloroform. The organic layer is washed with water and dried over anhydrous magnesium sulfate. Then, the solvent is distilled off. The residue is subjected to column chromatography and the eluate is converted into its maleate, which is recrystallized from a mixed solvent of methanol and isopropyl ether to give 7.2 g of 9-(3-dimethylaminopropoxy)-2-(4-methylphenyl)-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one.maleate, m.p. 159°-162° C.

Workup

  1. additionis added
  2. stirringAfter stirring at room temperature for 1 hour
  3. stirringAfter the mixture is stirred over water bath
  4. temperatureunder heating at 40°-50° C. for 5 hours
  5. extractionfollowed by extraction with chloroform
  6. washThe organic layer is washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThen, the solvent is distilled off
  9. customis recrystallized from a mixed solvent of methanol and isopropyl ether

Sources & evidence

ORD record
ord-ae430a858fdb499091bf16abd253a153
Source dataset
uspto-grants-1991_09
Patent number
US05045541

Reaction notes

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