Dimethylamine, hydrochloride → HCID 3078977, compound

HRID 727788Notes

Reaction equation

HRID 727788 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]2[CH2:6][CH2:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[N:12][N:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22](=O)[CH3:23])=[CH:16][CH:15]=1)[C:10](=[O:25])[CH:9]=3.Cl.[CH3:29][NH:30][CH3:31].C(B)#N.[Na]>C(O)C>[F:1][C:2]1[CH:27]=[CH:26][C:5]2[CH2:6][CH2:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[N:12][N:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]([N:30]([CH3:31])[CH3:29])[CH3:23])=[CH:16][CH:15]=1)[C:10](=[O:25])[CH:9]=3

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 19825008HCID 19825008, compoundHCID 101953985CID 101953985

Product 1

HCID 3078977HCID 3078977, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixture of 37 g of 9-fluoro-2-[4-(2-oxopropoxy)phenyl]-5,6-dihydrobenzo[h]cinnolin-3(2H)-one, 33 g of dimethylamine hydrochloride and 700 ml of ethanol is added dropwise 200 ml of an ethanol solution of 10 g of sodium cyanoboron hydride while stirring under heating and reflux over the period of 2 hours. After the completion of the dropwise addition, the reaction is concentrated under reduced pressure. To the residue is added 200 ml of water, and then conc. hydrochloric acid is added thereto under ice-cooling. After the mixture is stirred at room temperature for 1 hour, it is rendered alkaline with potassium carbonate and extracted with ethyl acetate. After the extract is washed with water and dried over magnesium sulfate, the solvent is distilled off under reduced pressure Ethanol is added to the thus obtained oily substance and further fumaric acid is added thereto to convert into its salt. The resultant crystals are recrystallized from hydrous ethanol to give 9-fluoro-2-[4-(2-dimethylaminopropoxy)phenyl]-5,6 -dihydrobenzo[h]cinnolin-3(2H)-one.fumarate.

Workup

  1. temperatureunder heating
  2. temperaturereflux over the period of 2 hours
  3. additionAfter the completion of the dropwise addition
  4. concentrationthe reaction is concentrated under reduced pressure
  5. additionTo the residue is added 200 ml of water
  6. additionconc. hydrochloric acid is added
  7. temperatureunder ice-cooling
  8. stirringAfter the mixture is stirred at room temperature for 1 hour
  9. extractionextracted with ethyl acetate
  10. washAfter the extract is washed with water
  11. dry with materialdried over magnesium sulfate
  12. distillationthe solvent is distilled off under reduced pressure Ethanol
  13. additionis added to the thus obtained oily substance and further fumaric acid
  14. additionis added
  15. customThe resultant crystals are recrystallized from hydrous ethanol

Sources & evidence

ORD record
ord-a8d729b207834f22bad47b96f07a8707
Source dataset
uspto-grants-1991_09
Patent number
US05045541

Reaction notes

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