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

HRID 2427228Notes

Reaction equation

HRID 2427228 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×

Procedure

To a solution of 3-Hydroxy-6-methylquinoline (308) (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 degrees with stirring for 2 hr. 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 309 (510 mg, 67%).

Workup

  1. temperaturethe reaction mixture was heated at 50 degrees
  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-f1e48f714e1e47dea29c0b2c0262ff59
Source dataset
uspto-grants-2011_06
Patent number
US07968567B2

Reaction notes

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