2-Aminophenol → 8-Quinolinol, 3-ethyl-

HRID 1195015Notes

Reaction equation

HRID 1195015 reaction equation
[CH2:1]([C:3](=[CH2:6])[CH:4]=O)[CH3:2].[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14].[N+](C1C=CC=CC=1O)([O-])=O.[OH-].[NH4+]>Cl.C(Cl)Cl>[CH2:1]([C:3]1[CH:4]=[N:7][C:8]2[C:13]([CH:6]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[OH:14])[CH3:2]

Participants

7

Reactant 4

HCID 58012-AminophenolHCID 69472-NitrophenolHCID 14923Ammonium HydroxideHCID 70203Ethylacrolein

Product 1

HCID 117896928-Quinolinol, 3-ethyl-

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

2-Ethylacrolein (161.5 g) is added over a two hour period to a stirred mixture of o-aminophenol (296 g, 1.0 mol) and o-nitrophenol in 37% aqeuous hydrochloric acid (296 g) at a temperature of 100° C. The reaction mixture is allowed to stir at 100° C. for two hours and is then cooled to room temperature. Methylene chloride is added to the cooled reaction mixture and the pH of the mixture is adjusted to pH 7.0 with concentrated ammonium hydroxide while stirring. The organic phase is removed and concentrated under reduced pressure. Vaccum distillation of the residue at 5 mm Hg collecting the distillate having a vapor temperature of 130° C. to 165° C. gives 3-ethyl-8-hydroxyquinoline of 93% to 98% purity as determined by assay using high performance liquid chromatograph.

Workup

  1. temperatureis then cooled to room temperature
  2. stirringwhile stirring
  3. customThe organic phase is removed
  4. concentrationconcentrated under reduced pressure
  5. distillationVaccum distillation of the residue at 5 mm Hg
  6. distillationcollecting the distillate
  7. customa vapor temperature of 130° C. to 165° C.

Sources & evidence

ORD record
ord-179a2b12032c430390db0774440371dd
Source dataset
uspto-grants-1989_03
Patent number
US04816588

Reaction notes

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