Ethanol → 4-(alpha-Carboxy-3,4-methylenedioxybenzyl)amino-6-chloroquinazoline

HRID 1900660Notes

Reaction equation

HRID 1900660 reaction equation
C(O)C.[OH-].[Na+].C([O:8][C:9]([CH:11]([NH:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([Cl:32])[CH:30]=2)[N:25]=[CH:24][N:23]=1)[C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1)=[O:10])C>O>[C:9]([CH:11]([NH:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([Cl:32])[CH:30]=2)[N:25]=[CH:24][N:23]=1)[C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1)([OH:10])=[O:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 18796707HCID 18796707, compound

Product 1

HCID 187966624-(alpha-Carboxy-3,4-methylenedioxybenzyl)amino-6-chloroquinazolineYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 ml of ethanol, 5 ml of water and 20 mg of sodium hydroxide were added to 100 mg of 4-(α-ethoxycarbonyl-3,4-methylenedioxybenzyl)amino-6-chloroquinazoline. The obtained mixture was refluxed for 10 minutes and concentrated under a reduced pressure, followed by the addition of 20 ml of water. The obtained mixture was neutralized with 1N hydrochloric acid. The crystal thus precipitated was recovered by filtration. Thus, 45 mg of the title compound was obtained.

Workup

  1. temperatureThe obtained mixture was refluxed for 10 minutes
  2. concentrationconcentrated under a reduced pressure
  3. additionfollowed by the addition of 20 ml of water
  4. customThe crystal thus precipitated
  5. filtrationwas recovered by filtration

Sources & evidence

ORD record
ord-5f9dadb471e8438990b755cca540b1b5
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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