2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 9-Benzyl-5-carbamoyl-4-methoxy-1-fluorocarbazole

HRID 567360Notes

Reaction equation

HRID 567360 reaction equation
[CH2:1]([N:8]1[C:20]2[CH2:19][CH2:18][CH2:17][CH:16]([C:21]([NH2:23])=[O:22])[C:15]=2[C:14]2[C:9]1=[C:10]([F:26])[CH:11]=[CH:12][C:13]=2[O:24][CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH2:1]([N:8]1[C:9]2[C:10]([F:26])=[CH:11][CH:12]=[C:13]([O:24][CH3:25])[C:14]=2[C:15]2[C:20]1=[CH:19][CH:18]=[CH:17][C:16]=2[C:21](=[O:22])[NH2:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 22739268HCID 22739268, compound

Product 1

HCID 227402909-Benzyl-5-carbamoyl-4-methoxy-1-fluorocarbazoleYield 99.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.458 g of 9-benzyl-5-methoxy-8-fluoro-1,2,3,4-tetrahydrocarbazole-4-carboxamide in 13 ml of dry dioxane under nitrogen was treated with 0.59 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and refluxed for one hour. The reaction mixture was cooled and filtered and the precipitate was washed with 15 ml of dioxane. The filtrate and washing were poured into saturated sodium bicarbonate solution and extracted three times with ethyl acetate. The extracts were washed with saturated sodium bicarbonate, with water and then with brine; dried over magnesium sulfate and concentrated. This residue was chromatographed on silica gel using dichloromethane/0-2% methanol to afford 0.45 g of subtitle compound. ESIMS m/e 349 (M++1)

Workup

  1. temperaturerefluxed for one hour
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. washthe precipitate was washed with 15 ml of dioxane
  5. washThe filtrate and washing
  6. additionwere poured into saturated sodium bicarbonate solution
  7. extractionextracted three times with ethyl acetate
  8. washThe extracts were washed with saturated sodium bicarbonate, with water
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customThis residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-38c857a142e44956a20e4f5f3acd1262
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Reaction notes

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