Benzoyl Peroxide → Methyl 3-(bromomethyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylate

HRID 1887816

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[N:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:7]2[C:12]([C:13](=[O:16])[C:14]=1[CH3:15])=[CH:11][CH:10]=[C:9]([Cl:17])[CH:8]=2)=[O:4].[Br:24]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:7]2[C:12]([C:13](=[O:16])[C:14]=1[CH2:15][Br:24])=[CH:11][CH:10]=[C:9]([Cl:17])[CH:8]=2)=[O:4]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 7-chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (1.6 g, 4.88 mmol), N-bromosuccinimide (869 mg, 4.88 mmol) and benzoyl peroxide (118 mg, 0.488 mmol) in carbon tetrachloride (50 mL) was heated at 100° C. for 5 hr. At this time, the reaction was cooled to 25° C. The resulting solids were collected by filtration to afford 3-bromomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (1.7 g, 85.6%) as a white solid. The material was used without further purification.

Workup

filtrationThe resulting solids were collected by filtration

Sources & evidence

ORD record: ord-f23da11f97e845d7838a4bd3b97937a9
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501732B2

Linked notes

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