4-Ethoxy-m-anisic acid → 1-(4-Ethoxy-3-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinol

HRID 585363

Reaction equation

HRID 585363 reaction equation
[CH3:1][CH:2]1[CH2:11][CH:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[CH2:13]([O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][C:17]=1[O:25][CH3:26])[CH3:14].C(OC1C=CC(C(O)=O)=CC=1OC)C>N1C=CC=CC=1>[CH2:13]([O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:10]([OH:12])[CH2:11][CH:2]2[CH3:1])=[O:21])=[CH:18][C:17]=1[O:25][CH3:26])[CH3:14]

Participants

5

Reactant 3

HCID 770694-Ethoxy-m-anisic acidHCID 1476341,2,3,4-Tetrahydro-2-methyl-4-quinolinolHCID 128431534-Ethoxy-3-methoxybenzoyl chloride

Product 1

HCID 223392011-(4-Ethoxy-3-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinolYield 30%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Methyl-1,2,3,4-tetrahydro-4-quinolinol (7.1 g, 43.5 mmol) synthesized in the published manner was dissolved in pyridine (50 ml), followed by addition of 4-ethoxy-3-methoxybenzoyl chloride prepared from 4-ethoxy-3-methoxybenzoic acid (9.2 g, 46.4 mmol). After stirring at room temperature for 16 hours, the reaction mixture was concentrated and extracted by addition of ethyl acetate and water. After the organic layer was dried and concentrated, the residue was applied to silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/1) and the resulting eluate was recrystallized from ethyl acetate-hexane to give the titled compound (4.4 g, yield: 30%) as a white crystal.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. extractionextracted by addition of ethyl acetate and water
  3. customAfter the organic layer was dried
  4. concentrationconcentrated
  5. customthe resulting eluate was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-3cc5cfec28264839b428a7fea88b71be
Source dataset
uspto-grants-2005_08
Patent number
US06930104B2

Linked notes

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