Hydrogen Bromide → HCID 19808708, compound

HRID 374038Notes

Reaction equation

HRID 374038 reaction equation
Br.[CH2:2]([N:4]([CH2:29][CH3:30])[CH2:5][CH2:6][N:7]1[C:23](=[O:24])[C:22]2[C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([O:25]C)[CH:19]=4)[NH:14][C:13]=3[C:12]([CH2:27][CH3:28])=[CH:11][C:10]=2[C:8]1=[O:9])[CH3:3].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:29]([N:4]([CH2:2][CH3:3])[CH2:5][CH2:6][N:7]1[C:23](=[O:24])[C:22]2[C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([OH:25])[CH:19]=4)[NH:14][C:13]=3[C:12]([CH2:27][CH3:28])=[CH:11][C:10]=2[C:8]1=[O:9])[CH3:30]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 19808824HCID 19808824, compound

Product 1

HCID 19808708HCID 19808708, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.0 ml of an aqueous 47% hydrobromide solution was added to 80 mg of N-(2-diethylaminoethyl)-1-ethyl-6-methoxycarbazole-3,4-dicarboximide. The mixture was refluxed for 40 minutes. Thereto was added 30 ml of water. The resulting mixture was adjusted to pH 9 with potassium carbonate, and extracted with 50 ml of ethyl acetate. The extract was washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from isopropyl alcohol to obtain 35 mg (yield: 45%) of N-(2-diethylaminoethyl)-1-ethyl-6-hydroxycarbazole-3,4-dicarboximide as yellow crystals.

Workup

  1. temperatureThe mixture was refluxed for 40 minutes
  2. extractionextracted with 50 ml of ethyl acetate
  3. washThe extract was washed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe residue was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-9b3ba39b0f7f445b9adcdabba17dbe2c
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

Loading…