Water → HCID 59843000, compound

HRID 1878774Notes

Reaction equation

HRID 1878774 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2.[C:14]1([C:20]2[CH:21]=[CH:22][C:23](=[O:26])[NH:24][N:25]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[K+].O>C1C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:14]1([C:20]2[CH:21]=[CH:22][C:23](=[O:26])[N:24]([CH2:2][CH2:3][C:4]3[CH:5]=[C:6]4[C:11](=[CH:12][CH:13]=3)[N:10]=[CH:9][CH:8]=[CH:7]4)[N:25]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 751063-Phenyl-6-pyridazoneHCID 68811984HCID 68811984, compound

Product 1

HCID 59843000HCID 59843000, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 241BenzeneSolvent

Conditions

Temperature
25 °C

Procedure

(reference: Synthesis 1981, 631). To a solution containing 6-(2-bromoethyl)quinoline (0.13 g, 0.56 mmol) in benzene (6.0 mL) was added 6-phenyl-3(2H)-pyridazinone (0.096 g, 0.56 mmol, Aldrich), tetrabutylammonium bromide (0.036 g, 0.11 mmol) and potassium hydroxide (0.094 g, 1.7 mmol). The mixture was stirred at 25° C. for 20 h, then poured into water (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 to 3.0% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound as a white solid (0.12 g, 63% yield). MS (ESI pos. ion) m/z (MH+): 328. Calc'd exact mass for C21H17N3O: 327. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.83 (dd, J=4.2, 1.7 Hz, 1 H), 8.25 (dd, J=8.3, 0.9 Hz, 1 H), 7.98 (d, J=9.8 Hz, 1 H), 7.94 (d, J=8.6 Hz, 1 H), 7.78 (d, J=1.4 Hz, 1 H), 7.65-7.71 (m, 3H), 7.47 (dd, J=8.3, 4.2 Hz, 1 H), 7.36-7.42 (m, 3 H), 7.02 (d, J=9.8 Hz, 1 H), 4.51 (t, J=7.2 Hz, 2 H), 3.31 (t, J=7.0 Hz, 2 H).

Workup

  1. custom(reference: Synthesis 1981, 631)
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined extracts were washed with brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated onto silica
  6. customPurification by silica gel chromatography (0 to 3.0% MeOH (2 M in NH3)/CH2Cl2)

Sources & evidence

ORD record
ord-c3ef1a9d08e24ac9b6a73c5a25d29537
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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