Diethyl Ether → 1-[1-(2,4-Dimethoxybenzyl)-4-(3-fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinolin-3-yl]pyridinium chloride

HRID 1169693Notes

Reaction equation

HRID 1169693 reaction equation
[Cl:1][CH2:2][C:3]([N:5]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=1[O:32][CH3:33])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[C:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=1)=[O:4].CCO[CH2:37][CH3:38]>N1C=CC=CC=1>[Cl-:1].[CH3:33][O:32][C:25]1[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=[CH:29][C:24]=1[CH2:23][N:5]1[C:6]2[C:7](=[CH:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=2)[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[C:2]([N+:5]2[CH:38]=[CH:37][CH:8]=[CH:7][CH:6]=2)[C:3]1=[O:4]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 687184392-chloro-N-(2,4-dimethoxybenzyl)-N-[2-(3-fluorobenzoyl)-4-methoxyphenyl]acetamide

Product 1

HCID 866117061-[1-(2,4-Dimethoxybenzyl)-4-(3-fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinolin-3-yl]pyridinium chloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-chloro-N-(2,4-dimethoxybenzyl)-N-[2-(3-fluorobenzoyl)-4-methoxyphenyl]acetamide (229 mg, 0.485 mmol) in 3 mL of pyridine was heated to reflux. A precipitate formed while the mixture stirred overnight. After cooling the mixture to room temperature, ether was added (10 mL), and the mixture was cooled further using an ice bath. The suspension was filtered, and the filtrate was washed with cold ether and dried in vacuo to provide the titled salt as a dark brown solid which was used in the next step without further purification. HRMS (ES) exact mass calculated for C30H25FN2O4 (M+): 497.1871. Found 497.1884.

Workup

  1. customA precipitate formed while the mixture
  2. temperaturethe mixture was cooled further
  3. filtrationThe suspension was filtered
  4. washthe filtrate was washed with cold ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-07906fced98a4550aa41d4afa14e3aad
Source dataset
uspto-grants-2010_11
Patent number
US07825131B2

Reaction notes

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