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4-Fluorobenzaldehyde → Ethyl 3-(4-fluorophenyl)-2-(4-(1-methylpyrrolidin-2-yl)phenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1968147
Notes
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Reaction equation

HRID 1968147 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]1[CH:24]=[CH:23][C:10](/[CH:11]=[N:12]/[C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][O:16][C:17]3=[O:22])=[CH:9][CH:8]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]=O)=[CH:28][CH:27]=1.[CH3:34][CH2:35][O-:36].[Na+]>C(OCC)(=O)CC.CCO>[F:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]2[C:35](=[O:36])[C:34]3[C:18]([C:17]([O:16][CH2:15][CH3:14])=[O:22])=[CH:19][CH:20]=[CH:21][C:13]=3[NH:12][CH:11]2[C:10]2[CH:23]=[CH:24][C:7]([CH:3]3[CH2:4][CH2:5][CH2:6][N:2]3[CH3:1])=[CH:8][CH:9]=2)=[CH:28][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 2723922Sodium ethoxideHCID 178480145HCID 178480145, compound

Product 1

HCID 67261804Ethyl 3-(4-fluorophenyl)-2-(4-(1-methylpyrrolidin-2-yl)phenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 42.3%

Reagents, catalysts & solvents 2

HCID 702Ethanol
Solvent
HCID 7749Ethyl PropionateSolvent

Procedure

A mixture of (E)-4-(4-(1-methylpyrrolidin-2-yl)benzylideneamino)isobenzofuran-1(3H)-one (0.32 g, 1 mmol), 4-fluorobenzenaldehyde (0.248 g, 2 mmol) was dissolved in dry ethyl propionate (5 mL), EtONa (0.136 g, 2 mmol) in EtOH (5 mL) was added to this solution and the mixture was stirred at room temperature until the starting material was disappeared as monitored by TLC. The reaction was quenched with 0.5 mL of water, the resulting mixture was concentrated in vacuo, and the residue was purified by column chromatography (MeOH:DCM=1:20) to give the title compound (200 mg, yield 42%) as a pale yellow solid. LC-MS (ESI) m/z: 472 (M+1)+.

Workup

  1. customThe reaction was quenched with 0.5 mL of water
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. customthe residue was purified by column chromatography (MeOH:DCM=1:20)

Sources & evidence

ORD record
ord-4ee3077c2156419ebf7101a06232eb48
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08420650B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes