Pentane → HCID 178487890, compound

HRID 394974Notes

Reaction equation

HRID 394974 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1C(O)=O.CCCCC>C1(OC2C=CC=CC=2)C=CC=CC=1>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8003PentaneHCID 2552894-HYDROXY-6-METHOXYQUINOLINE-3-CARBOXYLIC ACID

Product 1

HCID 178487890HCID 178487890, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of 53.5 g of 4-hydroxy-6-methoxyquinoline-3-carboxylic acid in 1000 cm3 of diphenyl ether was heated with stirring, at a temperature of between 250° C. and 260° C., for 2 hours 45 minutes. The reaction mixture was cooled to about 20° C. After stirring for 16 hours at this temperature, the mixture was poured with stirring into 1 liter of pentane and then filtered. The cake obtained was washed with 3 times 100 cm3 of pentane and then with 3 times 100 cm3 of diisopropyl ether. After drying in air, 37 g of 4-hydroxy-6-methoxyquinoline were obtained in the form of a beige-colored solid.

Workup

  1. temperaturewas heated
  2. stirringAfter stirring for 16 hours at this temperature
  3. additionthe mixture was poured
  4. filtrationfiltered
  5. customThe cake obtained
  6. washwas washed with 3 times 100 cm3 of pentane
  7. customAfter drying in air

Sources & evidence

ORD record
ord-e3fa0c46900d4ba8b122b03b80f24387
Source dataset
uspto-grants-2003_08
Patent number
US06603005B2

Reaction notes

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