2-Aminophenol → 4-Methyl-8-quinolinol

HRID 1905384Notes

Reaction equation

HRID 1905384 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH:9]([C:11]([CH3:13])=O)=[CH2:10].[OH-].[Na+]>Cl>[CH3:13][C:11]1[C:7]2[C:2](=[C:3]([OH:8])[CH:4]=[CH:5][CH:6]=2)[N:1]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 6570Methyl vinyl ketoneHCID 14798Sodium Hydroxide

Product 1

HCID 3451694-Methyl-8-quinolinolYield 13.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 100 ml of concentrated hydrochloric acid, 27.3 g (250 mmol) of 2-aminophenol and 41 ml (500 mmol, 2 eq.) of methyl vinyl ketone was heated to 110°-120° C. for 18 hours. The reaction was cooled, poured onto crushed ice, brought to pH 7 using 10N sodium hydroxide and extracted with ethyl acetate. The organic layers were washed with water, brine, dried (magnesium sulfate) and concentrated in vacuo. Purification by flash chromatography (silica gel, 1:2 ethyl acetate/petroleum ether) and crystallization (ethyl acetate) gave 5.3 g of the title compound as a light yellow solid: melting point 135°-136° C.

Workup

  1. temperatureThe reaction was cooled
  2. additionpoured
  3. customonto crushed ice
  4. extractionextracted with ethyl acetate
  5. washThe organic layers were washed with water, brine
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated in vacuo
  8. customPurification
  9. customby flash chromatography (silica gel, 1:2 ethyl acetate/petroleum ether) and crystallization (ethyl acetate)

Sources & evidence

ORD record
ord-e6d41a44818b4b27b4994ac408509984
Source dataset
uspto-grants-1989_06
Patent number
US04843082

Reaction notes

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