Ethanol → HCID 22004351, compound

HRID 324351Notes

Reaction equation

HRID 324351 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([Cl:19])[CH:17]=2)[C:12](Cl)=[N:11][N:10]=1.[CH2:26]([OH:28])[CH3:27]>>[Cl:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[C:12]([O:28][CH2:26][CH3:27])=[N:11][N:10]=[C:9]2[NH:8][CH2:7][C:6]1[CH:21]=[CH:22][C:23]([O:24][CH3:25])=[C:4]([Cl:3])[CH:5]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 10761565HCID 10761565, compound

Product 1

HCID 22004351HCID 22004351, compound

Conditions

Temperature
150 °C

Procedure

A solution of 120 mg of 60% oily sodium hydride in 20 ml of ethanol was added to 1.0 g of 4-(3-chloro-4-methoxybenzyl)amino-1,6-dichlorophthalazine prepared in Example 27. The obtained mixture was heated at 150° C. in a sealed tube overnight, cooled and concentrated in a vacuum. The residue was dissolved in ethyl acetate. The obtained solution was washed with water and a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and concentrated in a vacuum. The obtained residue was subjected to silica gel column chromatography and eluted with dichloromethane/methanol (50:1) to give 0.9 g of the title compound.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in a vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washThe obtained solution was washed with water
  5. dry with materiala saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in a vacuum
  7. washeluted with dichloromethane/methanol (50:1)

Sources & evidence

ORD record
ord-17a7a3e8b03b438390502a9edacf6085
Source dataset
uspto-grants-2001_04
Patent number
US06218392B1

Reaction notes

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