Hydrochloric Acid → 3-Nitrocarbazole

HRID 1517956Notes

Reaction equation

HRID 1517956 reaction equation
C1(S(CC[N:12]2[C:24]3[CH:23]=[CH:22][C:21]([N+:25]([O-:27])=[O:26])=[CH:20][C:19]=3[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)(=O)=O)C=CC=CC=1.[K].CC(C)([O-])C.C(OCC)(=O)C.Cl>O1CCCC1>[N+:25]([C:21]1[CH:22]=[CH:23][C:24]2[NH:12][C:13]3[C:18]([C:19]=2[CH:20]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3)([O-:27])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 50987170Potassium tertbutoxide3×HCID 59335116HCID 59335116, compound

Product 1

HCID 765033-Nitrocarbazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.2 g 9-(2-phenylsulphonyl-ethyl)-3-nitro-9H-carbazole are dissolved in 40 ml of tetrahydrofuran, combined with 700 mg potassium-tert.-butoxide and stirred for 2 hours at ambient temperature. A further 100 mg potassium-tert.-butoxide are added and the mixture is stirred for 4 hours at ambient temperature. Then another 100 mg potassium-tert.-butoxide are added. The mixture is heated for 2 hours to 50° C., divided between ethyl acetate and 1 N hydrochloric acid, the organic phase is washed with saturated sodium chloride solution and dried with magnesium sulphate. After elimination of the solvents in vacuo the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10 to 80:20).

Workup

  1. stirringthe mixture is stirred for 4 hours at ambient temperature
  2. temperatureThe mixture is heated for 2 hours to 50° C.
  3. washthe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried with magnesium sulphate
  5. customAfter elimination of the solvents in vacuo the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10 to 80:20)

Sources & evidence

ORD record
ord-e68b5d46086144fbbfd8f05ec7001ff1
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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