4-Chloro-6,7-dimethoxyquinoline → 6-Methyl-2-pyridinecarboxaldehyde

HRID 228645

Reaction equation

HRID 228645 reaction equation
ClC1C2C(=CC(OC)=C(OC)C=2)N=CC=1.O[C:17]1[C:18]([CH:24]=[O:25])=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:23][C:20]1[N:19]=[C:18]([CH:24]=[O:25])[CH:17]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 124219863-Hydroxy-6-methylpyridine-2-carbaldehyde

Product 1

HCID 707376-Methyl-2-pyridinecarboxaldehydeYield 13.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
150 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (330 mg), 3-hydroxy-6-methyl-2-pyridinecarbaldehyde (200 mg), and 4-dimethylaminopyridine (360 mg) were suspended in o-dichlorobenzene (7 ml), and the suspension was stirred at 150° C. for 3 hr. The reaction solution was cooled to room temperature and was then purified by column chromatography using acetone-chloroform to give 3-[6,7-dimethoxy-4-quinolyl]oxy}-6-methyl-2-pyridinecarbaldehyde (24 mg, yield 5%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-4db4ba8d7bab46529eeeeb2c47d6995c
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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