Ethanol → HCID 69134270, compound

HRID 969498Notes

Reaction equation

HRID 969498 reaction equation
Br[C:2]1[C:3]2[CH2:4][CH2:5][CH:6]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH:7][C:8]=2[C:9]2[N:14]=[C:13]([CH3:15])[N:12]([CH3:16])[C:10]=2[CH:11]=1.C1(P([C:36]2[CH:41]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C]=[O:43].O.[CH2:45]([OH:47])C>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:15][C:13]1[N:12]([CH3:16])[C:10]2[CH:11]=[C:2]([C:45]([O:47][CH2:41][CH3:36])=[O:43])[C:3]3[CH2:4][CH2:5][CH:6]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[NH:7][C:8]=3[C:9]=2[N:14]=1

Participants

8

Reactant 5

HCID 702EthanolHCID 962WaterHCID 11776TriphenylphosphineHCID 69134440HCID 69134440, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 69134270HCID 69134270, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of 5.0 g (14 mmol) 5bromo-2,3-dimethyl-8-phenyl-6,7,8,9-tetrahydro-3H-imidazo[4,5-h]-quinoline in 71 ml ethanol and 12 ml triethylamine were added 0.47 g (2.1 mmol) palladium(II) acetate and 1.8 g (6.9 mmol) triphenylphosphine. The mixture was transferred to an autoclave and carbonylated (6 bar carbon monoxide pressure, 100° C.) for 18 h. The reaction mixture was cooled down, poured into water and extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (dichloromethane/methanol=13:1). Crystallization from ethyl acetate/light petroleum ether yielded 3.22 g (66%) of the title compound as a colourless solid. m.p. 185-186° C.

Workup

  1. customfor 18 h
  2. temperatureThe reaction mixture was cooled down
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel (dichloromethane/methanol=13:1)
  8. customCrystallization from ethyl acetate/light petroleum ether

Sources & evidence

ORD record
ord-a55b83244a3045ada27134d0afdce2d7
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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