Dimethylformamide → HCID 66677988, compound

HRID 512584Notes

Reaction equation

HRID 512584 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]2[C:14](=[O:15])[CH2:13][CH2:12][CH2:11][C:10]2=[O:16])=[C:4]([CH3:17])[CH:3]=1.Cl[C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([Cl:29])[CH:25]=2)[N:20]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.Cl>[Cl:29][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][C:28]([O:1][C:2]1[CH:3]=[C:4]([CH3:17])[C:5]([CH:9]3[C:14](=[O:15])[CH2:13][CH2:12][CH2:11][C:10]3=[O:16])=[C:6]([CH3:8])[CH:7]=1)=[CH:27]2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 6075022,6-DichloroquinolineHCID 66677844HCID 66677844, compound

Product 1

HCID 66677988HCID 66677988, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 2-(4-hydroxy-2,6-dimethylphenyl)cyclohexane-1,3-dione (0.200 g, 0.0009 mol), 2,6-dichloroquinoline (0.170 g, 0.0009 mol) and potassium carbonate (0.350 g, 0.0025 mol) is added N,N-dimethylformamide (3 ml), and the mixture is heated at 140° C. for 40 minutes under microwave irradiation. The reaction mixture is then diluted with ethyl acetate (20 ml) and 2M hydrochloric acid (20 ml), and the organic phase is separated, dried over magnesium sulfate and evaporated under reduced pressure. The crude product is purified by preparative reverse phase HPLC to afford 2-[4-(6-chloroquinolin-3-yloxy)-2,6-dimethylphenyl]cyclohexane-1,3-dione as a cream solid.

Workup

  1. customthe organic phase is separated
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe crude product is purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-3e1b852bdd7440c293e0cc1e45f3869f
Source dataset
uspto-grants-2015_08
Patent number
US09102642B2

Reaction notes

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