HCID 2268087, compound → Ethyl 7-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2061856Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]=[C:10]([C:16]([O:18]CC)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][CH:7]=1>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:16](=[O:18])[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][NH:8]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 250 °C

Procedure

Dowtherm (50 mL) was taken in double neck round bottom flask (100 mL) and heated to 250° C. in sand bath. At this temperature diethyl {[(3-bromophenyl)amino]methylidene}propanedioate (Intermediate 32, 10.0 g, 29.2 mmol) was added and the reaction temperature was maintained for another 1 h at 250° C. After completion of the reaction, the reaction mixture was cooled to room temperature, a white solid was collected by filtration and dried to yield 6.0 g (69.3%) ethyl 7-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate.

Workup

temperaturethe reaction temperature was maintained for another 1 h at 250° C
customAfter completion of the reaction
temperaturethe reaction mixture was cooled to room temperature
filtrationa white solid was collected by filtration
customdried

Sources & evidence

ORD record: ord-b7ac0fde9dae4106a4bf259ad72f08ac
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283361B2

Reaction notes

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