Hydrochloric Acid → 7-Chloro-2-phenylquinazolin-4(3H)-one

HRID 1163237Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:17]#[N:18])=[C:6]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1.[OH-:19].[Na+].OO.Cl>O>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5]([C:17](=[O:19])[NH:18][C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N:8]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of N-(5-chloro-2-cyanophenyl)benzamide (150 mg, 0.58 mmol) in H2O (5 mL) was added in sequence NaOH (100 mg, 2.5 mmol) and H2O2 (30% in H2O, 0.25 mL, 2.2 mmol). The reaction was heated to 80° C. for 24 h then cooled to rt and stirred at rt for 1d. Aq HCl (2 M, 6 mL) was added forming a thick precipitate that was collected by a filtration. The filter cake was washed with H2O several times affording the title compound as a creamy-white solid; MS (ES+): m/z 257.1 (100) [MH+]; HPLC: tR=3.34 min (OpenLynx, polar—5 min).

Workup

temperaturethen cooled to rt
customforming a thick precipitate that
filtrationwas collected by a filtration
washThe filter cake was washed with H2O several times

Sources & evidence

ORD record: ord-bd244d977ee9484395adf8d7243f519c
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820662B2

Reaction notes

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