Potassium Hydroxide → 6-Phenyl-2-(quinolin-6-ylmethyl)pyridazin-3(2H)-one

HRID 1878775Notes

Reaction equation

Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[C:13]1([C:19]2[CH:20]=[CH:21][C:22](=[O:25])[NH:23][N:24]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[K+].C([O-])(O)=O.[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1>[C:13]1([C:19]2[CH:20]=[CH:21][C:22](=[O:25])[N:23]([CH2:2][C:3]3[CH:4]=[C:5]4[C:10](=[CH:11][CH:12]=3)[N:9]=[CH:8][CH:7]=[CH:6]4)[N:24]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a 25 mL round-bottomed flask containing 6-(bromomethyl)quinoline (0.35 g, 1.6 mmol) was added benzene (10 mL), 6-phenyl-3(2H)-pyridazinone (0.15 g, 0.87 mmol, Aldrich), tetrabutylammonium bromide (0.056 g, 0.17 mmol) and potassium hydroxide (0.15 g, 2.6 mmol). The mixture was stirred at 25° C., then poured into aq. NaHCO3 (100 mL) and extracted with EtOAc (3×50 mL). The combined extracts were washed with brine (50 mL), dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (0.5 to 5.0% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound as a white solid (0.050 g, 18% yield). MS (ESI pos. ion) m/z (MH+): 314. Calc'd exact mass for C20H15N3O: 313. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.88 (dd, J=4.2, 1.7 Hz, 1 H), 8.38 (dd, J=8.4, 0.8 Hz, 1 H), 8.11 (d, J=9.6 Hz, 1 H), 8.01 (d, J=8.6 Hz, 1 H), 7.88-7.93 (m, 3 H), 7.78 (dd, J=8.8, 2.0 Hz, 1 H), 7.43-7.54 (m, 4H), 7.13 (d, J=9.8 Hz, 1 H), 5.54 (s, 2 H).

Workup

extractionextracted with EtOAc (3×50 mL)
washThe combined extracts were washed with brine (50 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated onto silica
customPurification by silica gel chromatography (0.5 to 5.0% MeOH (2 M in NH3)/CH2Cl2)

Sources & evidence

ORD record: ord-85eb5b70dc6d49679372c85059510f58
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314087B2

Reaction notes

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