Hydrochloric Acid → 3-(2,6-Dichloro-4-nitro-phenoxy)-6-methyl-quinoline

HRID 1370487Notes

Reaction equation

HRID 1370487 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH3:12])=[CH:7][CH:6]=2.[H-].[Na+].[Cl:15][C:16]1[CH:17]=[C:18]([N+:24]([O-:26])=[O:25])[CH:19]=[C:20]([Cl:23])[C:21]=1Cl.Cl>CN(C=O)C>[Cl:15][C:16]1[CH:17]=[C:18]([N+:24]([O-:26])=[O:25])[CH:19]=[C:20]([Cl:23])[C:21]=1[O:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH3:12])=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 883653,4,5-TrichloronitrobenzeneHCID 221488886-Methylquinolin-3-ol

Product 1

HCID 221488743-(2,6-Dichloro-4-nitro-phenoxy)-6-methyl-quinolineYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 3-Hydroxy-6-methylquinoline (92) (348 mg, 2.19 mmol) in DMF (3.5 mL), was added NaH (60% oil suspension, 90 mg, 2.25 mmol) in one portion at room temperature. After 5 min 3,4,5-trichloronitrobenzene (509 mg, 2.25 mmol) in DMF (2 mL) was added and the reaction mixture was heated at 50° C. with stirring for 2 h. After cooling to room temperature. Ice/water was added to the reaction mixture, which was then acidified with 2N HCl and extracted twice with AcOEt. Organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated. Crude residue was purified by column chromatography (hexane/AcOEt=4/1, 80 g of silica gel) to afford compound 93 (510 mg, 67%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted twice with AcOEt
  3. washOrganic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customCrude residue was purified by column chromatography (hexane/AcOEt=4/1, 80 g of silica gel)

Sources & evidence

ORD record
ord-797125f2cbd94c749120d02a8dc72cb7
Source dataset
uspto-grants-2003_06
Patent number
US06583157B2

Reaction notes

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