N,N'-Dimethylethylenediamine → HCID 70496784, compound

HRID 2408018Notes

Reaction equation

HRID 2408018 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:20]=[C:19](Br)[CH:18]=[CH:17][C:16]=1[Cl:22])[CH2:9][C:8]2([CH3:24])[CH3:23])=[O:4].[O:25]1[CH2:29][CH2:28][NH:27][C:26]1=[O:30].CNCCNC.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.[Cu]I>[Cl:22][C:16]1[CH:17]=[CH:18][C:19]([N:27]2[CH2:28][CH2:29][O:25][C:26]2=[O:30])=[CH:20][C:15]=1[CH:10]1[CH2:9][C:8]([CH3:24])([CH3:23])[C:7]2[C:12](=[CH:13][CH:14]=[C:5]([C:3]([OH:2])=[O:4])[CH:6]=2)[NH:11]1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 739492-OxazolidinoneHCID 70495304HCID 70495304, compound

Product 1

HCID 70496784HCID 70496784, compoundYield 49.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture solution of 2-(5-bromo-2-chloro-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (1.39 g, 3.53 mmol), oxazolidin-2-one (323 mg, 3.7 mmol), copper(I) iodide (135 mg, 0.71 mmol), N,N′-dimethyl-ethane-1,2-diamine (0.152 mL, 1.41 mmol), and potassium carbonate (1.46 g, 10.6 mmol) in acetonitrile (30 mL) was stirred at 90° C. for 72 h. Then the reaction mixture was cooled to room temperature. The reaction mixture was extracted with ethyl acetate (200 mL×2), washed with saturated aqueous ammonium chloride solution (50 mL×3) and brine (50 mL×2), dried over anhydrous sodium sulfate and then concentrated in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 30-50% ethyl acetate in petroleum ether) to afford 2-[2-chloro-5-(2-oxo-oxazolidin-3-yl)-phenyl]-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (0.7 g, 49%) as a white solid: MS (ESI) M+1=401.0.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (200 mL×2)
  2. washwashed with saturated aqueous ammonium chloride solution (50 mL×3) and brine (50 mL×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by ISCO combi-flash chromatography (gradient elution, 30-50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-6af4d5544ed44d5fa22f3194eeea0bd7
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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