Ammonia → Ethyl 2,6-dichloro-4-phenylquinoline-3-carboxylate

HRID 1497054Notes

Reaction equation

HRID 1497054 reaction equation
O=P(Cl)(Cl)[Cl:3].[CH2:6]([O:8][C:9]([C:11]1[C:12](=O)[NH:13][C:14]2[C:19]([C:20]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:18][C:17]([Cl:27])=[CH:16][CH:15]=2)=[O:10])[CH3:7].N>O>[CH2:6]([O:8][C:9]([C:11]1[C:12]([Cl:3])=[N:13][C:14]2[C:19]([C:20]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:18][C:17]([Cl:27])=[CH:16][CH:15]=2)=[O:10])[CH3:7]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 738703Ethyl 6-chloro-2-oxo-4-phenyl-1,2-dihydro-3-quinolinecarboxylate

Product 1

HCID 1714247Ethyl 2,6-dichloro-4-phenylquinoline-3-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

POCl3 (15 ml) was added to 6-chloro-2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester (3 g, 9.15 mmol) and refluxed for 1 h. Then the reaction mixture was cooled to room temperature and diluted with cold water and the pH was adjusted to 7 with ammonia solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated in vacuo to afford a crude residue which was purified by flash column chromatography (100-200 mesh silica, eluting with 5-10% ethyl acetate in hexane) to afford pure 2,6-dichloro-4-phenyl-quinoline-3-carboxylic acid ethyl ester (2 g, 63%) as pale yellow solid. LC-MS: 346 (M+H)+.

Workup

  1. temperaturerefluxed for 1 h
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford a crude residue which
  7. customwas purified by flash column chromatography (100-200 mesh silica, eluting with 5-10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-90bec080609046b5b16307b105bb7b44
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

Loading…