8-Bromoquinoline → 8-Acetylquinoline

HRID 1055938Notes

Reaction equation

HRID 1055938 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C([Sn](CCCC)(CCCC)[C:17]([O:19]CC)=[CH2:18])CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[C:17](=[O:19])[CH3:18])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 1401098-BromoquinolineHCID 619414Stannane, tributyl(1-ethoxyethenyl)-

Product 1

HCID 122087898-AcetylquinolineYield 73%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 8-bromoquinoline (2.0 g, 9.661 mmol), tributyl(1-ethoxyvinyl)stannane (4.19 g, 11.59 mmol), and Pd(PPh3)4 (557 mg, 0.483 mmol) in toluene (50 mL) was heated under argon at 70° C. for 24 h. The mixture was cooled to RT and extracted with EtOAc (2×25 mL). The combined extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 30% EtOAc/petroleum ether) furnished 1-(quinolin-8-yl)ethanone (1.2 g, 7.01 mmol, 73% yield) as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ 8.99 (1H, dd, J=2 Hz & 2.4 Hz), 8.22 (1H, dd, J=2 Hz & 6.4 Hz), 7.95 (2H, d, J=7.6 Hz), 7.59 (1H, t, J=8 Hz), 7.48 (1H, dd, J=4 Hz), 2.95 (3H, s). m/z (ESI, +ve) 172.0 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to RT
  2. extractionextracted with EtOAc (2×25 mL)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customChromatographic purification of the residue (silica gel, 30% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-7963c12bcc8f466d8f2d72ed1384d629
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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