Cesium carbonate → 2-((Diphenylmethylene)amino)-5-methyl-5,6,7,8-tetrahydroquinolin-5-ol

HRID 1504887Notes

Reaction equation

HRID 1504887 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:8]([CH3:13])([OH:12])[CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+].[C:62](=[NH:75])([C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1>O1CCOCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+].[Cl-].[Na+].O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:63]1([C:62](=[N:75][C:2]2[CH:11]=[CH:10][C:9]3[C:8]([CH3:13])([OH:12])[CH2:7][CH2:6][CH2:5][C:4]=3[N:3]=2)[C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=2)[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1

Participants

10

Reactant 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 867317602-Chloro-5-methyl-5,6,7,8-tetrahydroquinolin-5-ol

Product 1

HCID 867317612-((Diphenylmethylene)amino)-5-methyl-5,6,7,8-tetrahydroquinolin-5-ol

Reagents, catalysts & solvents 5

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-5-methyl-5,6,7,8-tetrahydroquinolin-5-ol (306 mg, 1.55 mmol), Xantphos (107 mg, 0.185 mmol), tris(dibenzylideneacetone)dipalladium(0) (71 mg, 0.077 mmol), cesium carbonate (1.01 g, 3.09 mmol), and benzophenone imine (0.272 mL, 1.63 mmol) in 1,4-dioxane (10 ml) under an argon atmosphere was heated at 100° C. in an oil bath for 6 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (40 mL), saturated aqueous sodium bicarbonate solution (10 mL), and brine (20 mL). The layers were separated and the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (10-80% ethyl acetate/hexanes linear gradient) to afford 2-[(diphenylmethylidene)amino]-5-methyl-5,6,7,8-tetrahydroquinolin-5-ol. MS ESI calc'd. for C23H23N2O [M+H]+ 343. found 343.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (10-80% ethyl acetate/hexanes linear gradient)

Sources & evidence

ORD record
ord-f99d4bd5b723402ba3ff4e2a46e109ad
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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