Sodium Hydroxide → HCID 18796637, compound

HRID 1900666Notes

Reaction equation

HRID 1900666 reaction equation
[OH-:1].[Na+].[CH:3]([C:5]1[N:14]=[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]3[O:23][CH2:24][O:25][C:19]=3[CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:26][CH3:27])[CH:11]=2)[N:6]=1)=[O:4]>O1CCOCC1.[Ag-]=O>[C:3]([C:5]1[N:14]=[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]3[O:23][CH2:24][O:25][C:19]=3[CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:26][CH3:27])[CH:11]=2)[N:6]=1)([OH:1])=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18796659HCID 18796659, compound

Product 1

HCID 18796637HCID 18796637, compound

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

1.00 g of silver (I) oxide and 15 ml of a 1N aqueous solution of sodium hydroxide were added to a solution of 0.59 g (1.8 mmol) of the 2-formyl-4-(3,4-methylenedioxybenzyl)amino-6-methoxyquinazoline prepared in Example 141 in 20 ml of 1,4-dioxane. The obtained mixture was stirred at 60° C. After 30 minutes, the reaction mixture was filtered through Celite and the filter cake was washed with a small amount of dioxane and water. The filtrate and washings were neutralized with 1N hydrochloric acid and extracted with chloroform/ethanol. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under a reduced pressure to remove the solvent. The crystal thus formed was recovered by filtration and washed with chloroform to give 0.34 g of the title compound as a pale-yellow crystal.

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. washthe filter cake was washed with a small amount of dioxane and water
  3. extractionextracted with chloroform/ethanol
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationThe filtrate was distilled under a reduced pressure
  7. customto remove the solvent
  8. customThe crystal thus formed
  9. filtrationwas recovered by filtration
  10. washwashed with chloroform

Sources & evidence

ORD record
ord-868c3289877745a490583abf89ea70e0
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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