Boron trifluoride → HCID 136389335, compound

HRID 2422573Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:18]([CH3:19])[C:17](=[O:20])[C:16]3[C:11](=[C:12]([CH3:21])[CH:13]=[CH:14][CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1.B(F)(F)F.[OH-].[Na+]>ClCCl.C(OCC)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:18]([CH3:19])[C:17](=[O:20])[C:16]3[C:11](=[C:12]([CH3:21])[CH:13]=[CH:14][CH:15]=3)[N:10]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2-(4-Methoxyphenyl)-3,8-dimethyl-4(3H)-quinazolinone (2.02 g, 7.20 mmol) was dissolved in dichloromethane (10 ml), stirred at −78° C., then boron trifluoride (1.0 M in CH2 Cl2, 21.6 ml) was added thereto, gradually heated up to room temperature, and stirred at that temperature for 12 hours. The reaction solution was diluted with ethyl acetate, and with cooling with ice, this was poured into aqueous 1 N sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid and saturated saline water, and dried with magnesium sulfate. The organic layer was concentrated under reduced pressure to obtain the intended compound (1.54 g, 80%) as a pale yellow solid.

Workup

temperaturegradually heated up to room temperature
stirringstirred at that temperature for 12 hours
temperaturewith cooling with ice
extractionextracted with ethyl acetate
washThe organic layer was washed with 1 N hydrochloric acid and saturated saline water
dry with materialdried with magnesium sulfate
concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-9ee45a0b7a5840cf85aa0ff80a6626d5
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960394B2

Reaction notes

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