HCID 19808798, compound → HCID 19808811, compound

HRID 374036Notes

Reaction equation

HRID 374036 reaction equation
[CH3:1][N:2]([CH3:34])[CH2:3][CH2:4][N:5]1[C:21](=[O:22])[C:20]2[C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([O:23]CC5C=CC=CC=5)[CH:17]=4)[NH:12][C:11]=3[C:10]([O:31][CH2:32][CH3:33])=[CH:9][C:8]=2[C:6]1=[O:7].[H][H]>C(O)(=O)C.[C].[Pd]>[CH3:1][N:2]([CH3:34])[CH2:3][CH2:4][N:5]1[C:21](=[O:22])[C:20]2[C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([OH:23])[CH:17]=4)[NH:12][C:11]=3[C:10]([O:31][CH2:32][CH3:33])=[CH:9][C:8]=2[C:6]1=[O:7]

Participants

5

Reactant 2

HCID 19808798HCID 19808798, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19808811HCID 19808811, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

In 10 ml of acetic acid was dissolved 31 mg of N-(2-dimethylaminoethyl)-6-benzyloxy-1-ethoxycarbazole-3,4-dicarboximide. Thereto was added 30 mg of 5% palladium-carbon. The mixture was subjected to catalytic reduction in a hydrogen atmosphere at room temperature at atmospheric pressure. The resulting insoluble material was removed by filtration. The filtrate was subjected to distillation under reduced pressure to remove the solvent. The residue was mixed with 50 ml of ethyl acetate and 50 ml of an aqueous saturated sodium hydrogencarbonate solution. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous potassium carbonate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from ethanol to obtain 20 mg (yield: 80%) of N-(2-dimethylaminoethyl)-1-ethoxy-6-hydroxycarbazole-3,4-dicarboximide as orange crystals.

Workup

  1. customThe resulting insoluble material was removed by filtration
  2. distillationThe filtrate was subjected to distillation under reduced pressure
  3. customto remove the solvent
  4. additionThe residue was mixed with 50 ml of ethyl acetate and 50 ml of an aqueous saturated sodium hydrogencarbonate solution
  5. customThe organic layer was separated
  6. washwashed with an aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous potassium carbonate
  8. customThe solvent was removed by distillation under reduced pressure
  9. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-d4d96d0685fb47728549721ddd6627e7
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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