Hydrochloric Acid → 2-Methyl-4-phenylquinolin-8-ol

HRID 1604585Notes

Reaction equation

HRID 1604585 reaction equation
[OH:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)/[CH:10]=[CH:11]/[CH3:12].Cl.O.N>>[OH:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:3]=1[N:4]=[C:11]([CH3:12])[CH:10]=[C:9]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 58012-AminophenolHCID 231934Phenyl propenyl ketoneHCID 12896473Azane;hydrate

Product 1

HCID 196034182-Methyl-4-phenylquinolin-8-olYield 55.7%

Procedure

A mixture of 2-hydroxyaniline (2 g), crotonoylbenzene (8.03 g) and concentrated hydrochloric acid (8 ml) was refluxed for 24 hours. The mixture was neutralized with concentrated ammonia water under ice-cooling, and extracted with chloroform. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified according to a conventional manner to give 8-hydroxy-2-methyl-4-phenylquinoline (2.4 g) as an oil.

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperaturecooling
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified

Sources & evidence

ORD record
ord-94f642f325e0476c8ea84bc8f709a403
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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