Water → HCID 21183728, compound

HRID 1384823Notes

Reaction equation

HRID 1384823 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][C:7]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:6][C:5]=2[C:4]2[C:19]([CH2:30][C:31]#N)=[N:20][N:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:22](=[O:23])[C:3]1=2.[OH-:33].[K+].COCCO.[OH2:40]>>[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][C:7]([O:11][CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:6][C:5]=2[C:4]2[C:19]([CH2:30][C:31]([OH:40])=[O:33])=[N:20][N:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:22](=[O:23])[C:3]1=2

Participants

5

Reactant 4

HCID 962WaterHCID 80192-MethoxyethanolHCID 14797Potassium HydroxideHCID 21183756HCID 21183756, compound

Product 1

HCID 21183728HCID 21183728, compound

Procedure

A solution of 1.15 g (2.7 mmol) of 5-methyl-4-oxo-3-phenyl-8-(phenylmethoxy)-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetonitrile and of 1.54 g (39 mmol) of potassium hydroxide in a mixture of 10 ml of water and of 20 ml oF 2-methoxyethanol is heated at reflux. The mixture is extracted with dichloromethane, the aqueous phase is acidified and extracted with ethyl acetate, the organic phase is dried over sodium sulphate and the solvent is evaporated under reduced pressure. 0.38 g (0.86 mmol) of solid is isolated, which solid is used as is in the following stage.

Workup

  1. temperatureat reflux
  2. extractionThe mixture is extracted with dichloromethane
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-e3b0fbe53cad45b3958b3e3f253353d7
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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