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

HRID 1517993Notes

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 obtained in Step 3 (400 mg, 1.1 mmol) was suspended in dimethylformamide (DMF; 8 ml) and 2-bromoethyl acetate (152 μl, 1.4 mmol) and potassium carbonate (440 mg, 3.2 mmol) were added. The mixture was stirred with heating at 80° C. During the stirring, 2-bromoethyl acetate (152 μl, 1.4 mmol) was added twice and the mixture was stirred with heating at 80° C. for the total of 1.5 hrs. After allowing the mixture to cool, saturated aqueous ammonium chloride was added to the reaction solution, and the precipitate was collected by filtration, washed with water and vacuum-dried to give an object product (468 mg, yield 95%) as a white solid.

Workup

stirringthe mixture was stirred
temperaturewith heating at 80° C. for the total of 1.5 hrs
temperatureto cool
filtrationthe precipitate was collected by filtration
washwashed with water
customvacuum-dried

Sources & evidence

ORD record: ord-b5eb0fbab5d44c108a43769a7f4fb626
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232401B2

Reaction notes

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