Sodium Hydroxide → 6-Methylquinolin-3-OL

HRID 1865544Notes

Reaction equation

HRID 1865544 reaction equation
N[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH3:12])=[CH:7][CH:6]=2.N([O-])=[O:14].[Na+].[OH-].[Na+]>OS(O)(=O)=O.O>[OH:14][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH3:12])=[CH:7][CH:6]=2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 221488796-Methylquinolin-3-amineHCID 23668193Sodium Nitrite

Product 1

HCID 221488886-Methylquinolin-3-OLYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of 3-Amino-6-methylquinoline [(1.21 g, 7.65 mmol), prepared according to J. Chem. Soc. 2024-2027 (1948) Morley, J. S.; Simpson, J. C. E.] in 6N H2SO4 (25 ml) was cooled in an ice bath. To the solution NaNO2 (560 mg, 8.10 mmol) in water (2 ml) was added and stirred for 30 min at 0 degrees. Separately 5% H2SO4 was refluxed and above Diazo reaction mixture was added to this refluxing solution. After 30 min the reaction mixture was cooled to room temperature, and was neutralized by 6N NaOH. The resulting insoluble material was collected by filtration. This solid was recrystallized by CHCl3/AcOEt to afford compound (308) (348 mg, 29%).

Workup

  1. additionwas added to this refluxing solution
  2. filtrationThe resulting insoluble material was collected by filtration
  3. customThis solid was recrystallized by CHCl3/AcOEt

Sources & evidence

ORD record
ord-cd13ca1ffa774d5881330acd591e2763
Source dataset
uspto-grants-2009_12
Patent number
US07626033B2

Reaction notes

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