Sodium Hydroxide → Cinnolin-3(2H)-one

HRID 727785Notes

Reaction equation

HRID 727785 reaction equation
OC1C=C[C:5]2[CH2:6][CH2:7][CH:8]3[C:13]([C:4]=2C=1)=[N:12][N:11](C1C=CC(O)=CC=1)[C:10](=[O:21])[CH2:9]3.[OH-].[Na+].CN(C)CCCCl>CN(C)C=O>[N:12]1[NH:11][C:10](=[O:21])[CH:9]=[C:8]2[C:13]=1[CH:4]=[CH:5][CH:6]=[CH:7]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 14986982HCID 14986982, compound

Product 1

HCID 234722Cinnolin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 60 ml of dried dimethylformamide is added 5 g of 9-hydroxy-2-(4-hydroxyphenyl)-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one, and thereto is added 1.6 g of 60% sodium hydroxide. After the mixture is stirred at room temperature for 1 hour, 5 g of 3-dimethylaminopropyl chloride is added thereto. The mixture is stirred under heating at 60°-70° C. for 14 hours. After the completion of the reaction, the solvent is distilled off and the residue is extracted with chloroform. The extract is washed with water and dried over anhydrous magnesium sulfate. Thereafter, the solvent is distilled off. The obtained oily substance (7.8 g) is subjected to column chromatography to give 5.2 g of 2-[4-(3-dimethylaminopropoxy)phenyl]-9-(3-dimethylaminopropoxy)-4,4a,5,6-tetrahydrobenzoh]cinnolin-3(2H)-one as an oily substance.

Workup

  1. stirringThe mixture is stirred
  2. temperatureunder heating at 60°-70° C. for 14 hours
  3. customAfter the completion of the reaction
  4. distillationthe solvent is distilled off
  5. extractionthe residue is extracted with chloroform
  6. washThe extract is washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThereafter, the solvent is distilled off

Sources & evidence

ORD record
ord-fabb3f87969d4f1f8d68b54919c47542
Source dataset
uspto-grants-1991_09
Patent number
US05045541

Reaction notes

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