1,3-Propanediol → 2,2-dimethyl-2H-pyrano[2,3-g]quinoline

HRID 2425365Notes

Reaction equation

HRID 2425365 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:13])([CH3:12])[CH:6]=[CH:5]2.[CH2:14](O)[CH2:15][CH2:16]O.C(P(CCCC)CCCC)CCC>COCCOC.[Ru](Cl)(Cl)Cl>[CH3:12][C:7]1([CH3:13])[O:8][C:9]2=[CH:10][C:11]3[CH:14]=[CH:15][CH:16]=[N:1][C:2]=3[CH:3]=[C:4]2[CH:5]=[CH:6]1

Participants

6

Reactant 3

HCID 104421,3-PropanediolHCID 13831TributylphosphineHCID 100808812,2-Dimethyl-2H-chromen-6-amine

Product 1

HCID 591344202,2-dimethyl-2H-pyrano[2,3-g]quinolineYield 59%

Reagents, catalysts & solvents 2

HCID 61850Ruthenium trichlorideCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
180 °C

Procedure

Under nitrogen atmosphere, to a solution of 6-amino-2,2-dimethylchromene (3.88 g, 22.1 mmol) and ruthenium trichloride (55.0 mg, 0.265 mmol) in dimethylene glycol dimethyl ether (8 mL), 1,3-propanediol (0.639 mL, 8.84 mmol) and tri-n-butyl phosphine (0.132 mL, 0.530 mmol) were added at room temperature, and the resulting mixture was stirred at 180° C. for 5 hours. Upon the completion of the reaction, ruthenium complex was removed by florisil column, and solvent was distilled off. The residue was purified by medium pressure column chromatography (hexane/ethyl acetate=5/1) and the aimed product was obtained (yield: 59%).

Workup

  1. customUpon the completion of the reaction, ruthenium complex
  2. customwas removed by florisil column, and solvent
  3. distillationwas distilled off
  4. customThe residue was purified by medium pressure column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-4d7e4c30726541d6837b3dc08d988bbb
Source dataset
uspto-grants-2011_06
Patent number
US07964623B2

Reaction notes

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