Ethyl Acetate → 2-Methylquinoline

HRID 1604605Notes

Reaction equation

HRID 1604605 reaction equation
ClC1C(N(C(=O)COS(C)(=O)=O)C)=CC=C(Cl)C=1CO[C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2.NC1C=C(C2C=CC(C(N(C)C)=O)=CC=2)C=CC=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH3:16][C:13]1[CH:12]=[CH:11][C:10]2[C:15](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:14]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 196032903'-Amino-N,N-dimethyl[1,1'-biphenyl]-4-carboxamideHCID 19603383HCID 19603383, compound

Product 1

HCID 70602-MethylquinolineYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 8-[2,6-dichloro-3-(N-methanesulfonyloxyacetyl-N-methylamino)benzyloxy]-2-methylquinoline (110 mg), 4-(3-aminophenyl)-N,N-dimethylbenzamide (60.2 mg) and potassium carbonate (94.2 mg) in N,N -dimethylformamide (1 ml) was stirred for 12 hours at 60° C., and ethyl acetate and water were added thereto. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform:methanol=20:1, V/V) to give 8-[2,6-dichloro-3-methylamino]benzyloxy]-2-methylquinoline (30 mg) as colorless amorphous.

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative thin-layer chromatography (chloroform:methanol=20:1, V/V)

Sources & evidence

ORD record
ord-f06a43aa50bf4e399c3cee4f732cc3e0
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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