Hydroquinone → HCID 9823498, compound

HRID 1939306Notes

Reaction equation

HRID 1939306 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:14]3[N:13]([C:15]4[CH:20]=[CH:19][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:17][CH:16]=4)[N:12]=[C:11]([C:25]([F:28])([F:27])[F:26])[C:10]=3[CH2:9][CH2:8][C:7]=2[CH:29]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.C1(C=CC(O)=CC=1)O>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH:29]=1)=[CH:8][CH:9]=[C:10]1[C:14]=2[N:13]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[N:12]=[C:11]1[C:25]([F:28])([F:26])[F:27]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone3×HCID 9932059HCID 9932059, compound

Product 1

HCID 9823498HCID 9823498, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-[4,5-Dihydro-7-methoxy-3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide from Step 2 (1.27 g, 3.0 mmol) was dissolved in 1,4-dioxane (200 ml), and DDQ (681 mg, 3.0 mmol) was added. The reaction was heated to reflux for 16 hours at which time a second equivalent of DDQ (681 mg, 3.0 mmol) was added and the reaction was heated to reflux for an additional 24 hours. At three successive 24 hour intervals, 3.0 mmol additional DDQ was added and heating continued until no starting material was left (as determined by thin layer chromatography). The reaction was cooled to room temperature at which time most of the hydroquinone by-product precipitated. The reaction was filtered and concentrated. The residue was chromatographed on silica gel eluting with 50% ethyl acetate in hexane to yield 4-[7-methoxy-3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide (1.1 g, 87%): 1H NMR (acetone d6) δ=3.9 (s, 3H), 6.9 (broad s, 2H) 7.1 (m, 1H), 7.6 (m, 2H), 7.8 (m, 2H), 8.0 (d, 2H j=8.7 Hz), 8.2 (d, 2H j=8.7 Hz); 19F NMR (acetone d6) δ-61.8 ppm (s, 3F).

Workup

  1. temperatureThe reaction was heated
  2. additionwas added
  3. temperaturethe reaction was heated
  4. temperatureto reflux for an additional 24 hours
  5. temperatureheating
  6. waitwas left (as determined by thin layer chromatography)
  7. customprecipitated
  8. filtrationThe reaction was filtered
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica gel eluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ca8583fd942e48ca8e3b0522c483a250
Source dataset
uspto-grants-1997_12
Patent number
US05696143

Reaction notes

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