HCID 23078304, compound → 2-methylquinolin-3-ol

HRID 228837Notes

Reaction equation

HRID 228837 reaction equation
[OH:1][C:2]1[C:3]([CH3:17])=[N:4][C:5]2[C:10]([C:11]=1C(OCC)=O)=[CH:9][CH:8]=[CH:7][CH:6]=2>ClC1C=CC=CC=1Cl>[OH:1][C:2]1[C:3]([CH3:17])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

3

Reactant 1

HCID 23078304HCID 23078304, compound

Product 1

HCID 5943942-methylquinolin-3-olYield 67.5%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
150 °C

Procedure

Ethyl 3-hydroxy-2-methyl-quinoline-4-carboxylate (2.10 g) was suspended in o-dichlorobenzene (50 ml), and the mixture was stirred at 150° C. overnight and was further stirred at 160° C. for one day. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography using methanol-chloroform to give 3-hydroxy-2-methyl-quinoline (976 mg, yield 60%).

Workup

  1. stirringwas further stirred at 160° C. for one day
  2. temperatureThe reaction solution was cooled to room temperature
  3. customthe solvent was then removed by distillation under the reduced pressure
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f37257a7e5924385be5f772db4e8c07b
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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