4-Aminophenol → 6-Hydroxyquinoline

HRID 1890924Notes

Reaction equation

HRID 1890924 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.O[CH2:10][CH:11]([CH2:13]O)O.C1C([N+]([O-])=O)=CC=C(O)C=1.[OH-].[Na+]>S(=O)(=O)(O)O>[N:1]1[C:2]2[C:7](=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)[CH:13]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 753GlycerolHCID 9804-NitrophenolHCID 14798Sodium Hydroxide

Product 1

HCID 113746-HydroxyquinolineYield 42%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of 4-aminophenol (44.7 g, 0.41 mol), ferrous sulfate (14 g, 0.05 mol), glycerol (120 mL, 1.65 mol), p-nitrophenol (33.3 g, 0.24 mol), and concentrated sulfuric acid (20 mL) was heated gently to 70° C. Then a second portion of concentrated sulfuric acid (25 mL) was added dropwise to the reaction mixture and the mixture was stirred at reflux for 8 hours. After cooling down to room temperature, the reaction mixture was basified to pH=5.5 with 15% aqueous sodium hydroxide solution in an ice bath. The resulting precipitate was filtered, dried and 25 g of quinolin-6-ol was obtained as a yellow solid (42% yield).

Workup

  1. temperatureat reflux for 8 hours
  2. temperatureAfter cooling down to room temperature
  3. filtrationThe resulting precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-c5dcb2c41547482db90a5feab120b58c
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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