Pyridine → 3-(4-Oxo-3,4-dihydroquinazolin-2-yl)phenyl acetate

HRID 61529Notes

Reaction equation

HRID 61529 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:17][C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>>[C:25]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[NH:17][C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:3]=1)(=[O:27])[CH3:26]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 1355672462-(3-hydroxyphenyl)quinazolin-4(3H)-one

Product 1

HCID 1357964653-(4-Oxo-3,4-dihydroquinazolin-2-yl)phenyl acetate

Conditions

Temperature
105 °C

Procedure

To 2-(3-hydroxyphenyl)quinazolin-4(3H)-one (11.0 g, 45.98 mmole) was added pyridine (16.06 mL, 15.71 g, 0.199 mmole) followed by addition of acetic anhydride (145 mL) and the reaction mixture was heated to 105° C. and stirred for 3.5 h. The reaction mixture was cooled to ambient temperature and then poured onto ice-water (800 mL) and stirred for 2 h. The solid was then filtered and washed with water, ethanol, ether and finally hexane and dried for several hours under high vacuum to give 3-(4-oxo-3,4-dihydroquinazolin-2-yl)phenyl acetate. (8.4 g, mmol, 65%).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. additionpoured onto ice-water (800 mL)
  3. stirringstirred for 2 h
  4. filtrationThe solid was then filtered
  5. washwashed with water, ethanol, ether and finally hexane
  6. customdried for several hours under high vacuum

Sources & evidence

ORD record
ord-d26e9072e1304b089df97bd3baa2af61
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

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