Sodium Hydroxide → HCID 13387786, compound

HRID 483236Notes

Reaction equation

HRID 483236 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][CH2:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])[CH2:24][CH2:23]2)[C:10]1=[O:36])=[O:5])C.[OH-].[Na+]>C(O)C>[C:4]([CH2:6][CH2:7][CH2:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])[CH2:26][CH2:27]2)[C:10]1=[O:36])([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13387774HCID 13387774, compound

Product 1

HCID 13387786HCID 13387786, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 1-(3-ethoxycarbonylpropyl)3-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-2,4-(1H,3H)quinazolinedione (4.53 g) obtained in Example 7-c) was dissolved in ethanol (40 ml). After adding 2N aqueous sodium hydroxide under cooling with ice, the resulting mixture was stirred at room temperature for 3 hours. The solvent was distilled off under vacuum and the residue was dissolved in water (20 ml). When the pH of the solution was adjusted to 7 with 10% aqueous hydrochloric acid, a crystal formed. It was filtered off and recrystallized from a mixture of ethanol and n-hexane to provide pale yellow needles of 1-(3-carboxypropyl)-3-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-2,4-(1H,3H)quinazolinedione (2.52 g) with a m.p. of 182° C. (decomposed).

Workup

  1. temperatureunder cooling with ice
  2. distillationThe solvent was distilled off under vacuum
  3. dissolutionthe residue was dissolved in water (20 ml)
  4. customa crystal formed
  5. filtrationIt was filtered off
  6. customrecrystallized from a mixture of ethanol and n-hexane

Sources & evidence

ORD record
ord-da2adf6384cc4711945ae5da0d0bb406
Source dataset
uspto-grants-1986_03
Patent number
US04578465

Reaction notes

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