Potassium Carbonate → Ethyl 1-(2-acetoxyethyl)-6-(2,3-dichlorobenzyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 491517Notes

Reaction equation

[Cl:1][C:2]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:8]2=[O:20].[C:26]([O:29][CH2:30][CH2:31]Br)(=[O:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[C:26]([O:29][CH2:30][CH2:31][N:11]1[C:12]2[C:7](=[CH:6][C:5]([CH2:4][C:3]3[CH:21]=[CH:22][CH:23]=[C:24]([Cl:25])[C:2]=3[Cl:1])=[CH:14][CH:13]=2)[C:8](=[O:20])[C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10]1)(=[O:28])[CH3:27]

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl 6-(2,3-dichlorobenzyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate (400 mg, 1.1 mmol) obtained in Step 3 was suspended in dimethylformamide (DMF; 8 ml), 2-bromoethyl acetate (152 μl, 1.4 mmol) and potassium carbonate (440 mg, 3.2 mmol) were added, and the mixture was stirred with heating at 80° C. 2-Bromoethyl acetate (152 μl, 1.4 mmol) was added twice on the way, and the mixture was stirred with heating at 80° C. for 1.5 hr in total. After allowing to cool, saturated aqueous ammonium chloride was added to the reaction mixture, and the precipitated solid was collected by filtration, washed with water, and vacuum dried to give the object product (468 mg, yield 95%) as a white solid.

Workup

stirringthe mixture was stirred
temperaturewith heating at 80° C. for 1.5 hr in total
temperatureto cool
filtrationthe precipitated solid was collected by filtration
washwashed with water, and vacuum
customdried

Sources & evidence

ORD record: ord-4915396e966b4f0bb34f8fe36b0da60d
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531554B2

Reaction notes

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