Potassium Carbonate → 3-Quinolinol, 8-methoxy-

HRID 399744Notes

Reaction equation

HRID 399744 reaction equation
N[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[O:12][CH3:13].N([O-])=[O:15].[Na+].C(=O)([O-])[O-].[K+].[K+]>S(=O)(=O)(O)O.O>[OH:15][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[O:12][CH3:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 189450658-Methoxyquinolin-3-amine2×HCID 23668193Sodium Nitrite

Product 1

HCID 110843893-Quinolinol, 8-methoxy-

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

In 53 ml of 33%(v/v) sulfuric acid was dissolved 6.2 g of 3-amino-8-methoxy quinoline [compound (IV)]. The solution was cooled to 0° C., and to the solution was slowly dropped 2.6 g of sodium nitrite which is dissolved in 12 ml of water. The solution was agitated at 0° to 5° C. for 30 minutes. The resulting solution was dropped in 47 ml of 50%(v/v) which was kept 160° C., agitated for 1 hour, and cooled. To the solution was added 300 ml of water and neutralized with aqueous potassium carbonate. By filtering and drying the solid portion, 3.8 g of 3-hydroxy-8-methoxy quinoline [compound (V)], which is yellow-red, was obtained in a solid state.

Workup

  1. additionThe resulting solution was dropped in 47 ml of 50%(v/v) which
  2. customwas kept 160° C.
  3. stirringagitated for 1 hour
  4. temperaturecooled
  5. filtrationBy filtering
  6. dry with materialdrying the solid portion, 3.8 g of 3-hydroxy-8-methoxy quinoline [compound (V)], which
  7. customwas obtained in a solid state

Sources & evidence

ORD record
ord-aed8892c06554a4684b12ea2dbad7ce8
Source dataset
uspto-grants-1998_10
Patent number
US05824689

Reaction notes

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