Boron tribromide → 6-Hydroxy-2-(3-nitrophenyl)quinazolin-4(1H)-one

HRID 61631Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1)[NH:7][C:6]2=[O:22].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1)[NH:7][C:6]2=[O:22]

Participants

Conditions

Temperature: -78 °C

Procedure

To a suspension of 6-methoxy-2-(3-nitrophenyl)quinazolin-4(3H)-one (3.90 g, 13.1 mmol), in CH2Cl2 (30 mL) cooled to −78° C. under an atmosphere of N2 was added BBr3 as a 1.0M solution in CH2Cl2 (20 mL, 20.0 mmol). The resulting mixture was stirred at −78° C. for 1 h, then allowed to warm to RT upon which it was stirred for a further 3 h. The mixture was re-cooled to −78° C. and stirred overnight. The reaction was quenched by the addition of EtOH (60 mL) and allowed to warm to RT. Stirring was continued for 1 h at RT, upon which a precipitate formed. Sat. NaHCO3 solution was added and the yellow solid was collected via filtration and washed with Et2O and EtOH and dried under vacuum to give 6-hydroxy-2-(3-nitrophenyl)quinazolin-4(3H)-one (2.96 g, 10.5 mmol, 80%). HPLC retention time 5.588 min.

Workup

temperatureto warm to RT upon which it
stirringwas stirred for a further 3 h
temperatureThe mixture was re-cooled to −78° C.
stirringstirred overnight
customThe reaction was quenched by the addition of EtOH (60 mL)
temperatureto warm to RT
stirringStirring
waitwas continued for 1 h at RT, upon which
customa precipitate formed
filtrationthe yellow solid was collected via filtration
washwashed with Et2O and EtOH
customdried under vacuum

Sources & evidence

ORD record: ord-de86fd3010594254b61cb6f047996577
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440961B2

Reaction notes

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