Methanesulfonic Acid → 6,8-difluoro-N-methyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine

HRID 427158Notes

Reaction equation

HRID 427158 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.Cl.[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[NH:19]N.CS(O)(=O)=O>C(O)C>[CH3:1][NH:2][CH:3]1[CH2:8][C:7]2[C:14]3[C:13](=[C:12]([F:11])[CH:17]=[C:16]([F:18])[CH:15]=3)[NH:19][C:6]=2[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 27333012,4-Difluorophenylhydrazine hydrochlorideHCID 207606324-(Methylamino)cyclohexanone

Product 1

HCID 123618236,8-difluoro-N-methyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.5 g. of 4-methylaminocyclohexanone, 5.1 g. of 2,4-difluorophenylhydrazine hydrochloride, and 4 g. of methanesulfonic acid in 50 ml. of absolute ethyl alcohol was heated under reflux for four hours, cooled, and filtered. The resulting solids were washed with isopropanol and treated in chloroform with 10% potassium hydroxide solution. The chloroform extract was evaporated to dryness to give 3-(methylamino)-6,8-difluoro-1,2,3,4-tetrahydrocarbazole, m.p. 135°-138° C., which was converted to the hydrochloride salt, m.p. >280° C.

Workup

  1. temperatureunder reflux for four hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe resulting solids were washed with isopropanol
  5. additiontreated in chloroform with 10% potassium hydroxide solution
  6. extractionThe chloroform extract
  7. customwas evaporated to dryness

Sources & evidence

ORD record
ord-4c4c21e4cc4b4efcb1e9c206763efd41
Source dataset
uspto-grants-1979_10
Patent number
US04172834

Reaction notes

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