Sodium Hydroxide → 6-Methylquinolin-3-OL

HRID 1819765Notes

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

Conditions

Temperature: 0 °C

Procedure

A solution of 3-Amino-6-methylquinoline [(1.21 g, 7.65 mmol), prepared according to J. Chem. Soc. 2024-2027 (1948) Morley et al.] 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° C. 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 (92) (348 mg, 29%). 1H NMR (300 MHz, DMSO-d6) δ 7.34 (1H, dd, J=1.9, 8.6 Hz), 7.42 (1H, d, J=2.8 Hz), 7.55 (1H, s), 7.79 (1H, d, J=8.6 Hz), 8.50 (1H, d, J=2.8 Hz).

Workup

additionwas added to this refluxing solution
temperatureAfter 30 min the reaction mixture was cooled to room temperature
filtrationThe resulting insoluble material was collected by filtration
customThis solid was recrystallized by CHCl3/AcOEt

Sources & evidence

ORD record: ord-4a81d37c2b57460cae25ed957d939746
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601841B2

Reaction notes

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