4-Aminophenol → 2-ethyl-3-(4-hydroxyphenyl)-4-(3H)-quinazolinone

HRID 2386923Notes

Reaction equation

HRID 2386923 reaction equation
[CH2:1]([C:3]1O[C:7](=[O:9])[C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[N:4]=1)[CH3:2].[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1>CN(C)C=O>[CH2:1]([C:3]1[N:14]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[C:7](=[O:9])[C:6]2[C:5](=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 9285262-Ethyl-benzo[d][1,3]oxazin-4-one

Product 1

HCID 7113732-ethyl-3-(4-hydroxyphenyl)-4-(3H)-quinazolinoneYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

2-ethyl-4H-3,1-benzoxazin-4-one (6.5 g, 37.1 mmol) and 4-aminophenol (4.05 g, 37.1 mmol) were dissolved in dimethylformamide (18 mL) and stirred at 140° C. for 10 hours. After leaving to cool to room temperature, distilled water (94 mL) was added, and the solid precipitate was filtered off. The product was recrystallized (ethanol) and the target compound (6.52 g, 66%) was obtained as light brown crystals.

Workup

  1. customAfter leaving
  2. temperatureto cool to room temperature
  3. distillationdistilled water (94 mL)
  4. additionwas added
  5. filtrationthe solid precipitate was filtered off
  6. customThe product was recrystallized (ethanol)

Sources & evidence

ORD record
ord-b7d9c0b56f054245baa56458c6fd3246
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

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