Diisopropyl Ether → HCID 178486804, compound

HRID 394988Notes

Reaction equation

HRID 394988 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1C(O)=O.C(OC(C)C)(C)C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[OH:1]

Participants

4

Reactant 2

HCID 7914Diisopropyl EtherHCID 178486815HCID 178486815, compound

Product 1

HCID 178486804HCID 178486804, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
250 °C

Procedure

A mixture of 9.24 g of 4-hydroxy-6,7-dimethoxyquinoline-3-carboxylic acid in 185 cm3 of diphenyl ether was maintained, with mechanical stirring, at a temperature in the region of 250° C. for 1.3 hours. After cooling the reaction mixture to about 20° C., 100 cm3 of diisopropyl ether were added. The suspension was stirred for 8 hours and filtered, and the filter cake was washed with 3 times 100 cm3 of diisopropyl ether. 7.96 g of 6,7-dimethoxyquinolin-4-ol were obtained in the form of a brown solid.

Workup

  1. temperatureAfter cooling the reaction mixture to about 20° C.
  2. filtrationfiltered
  3. washthe filter cake was washed with 3 times 100 cm3 of diisopropyl ether

Sources & evidence

ORD record
ord-1b07b0afbef6461a8b68c0257cc4bb9a
Source dataset
uspto-grants-2003_08
Patent number
US06603005B2

Reaction notes

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