Water → HCID 6481894, compound

HRID 374027Notes

Reaction equation

HRID 374027 reaction equation
[CH3:1][N:2]([CH3:27])[CH2:3][CH2:4][N:5]1[C:21](=[O:22])[C:20]2[C:19]3[C:18]4[C:13](=[CH:14][C:15]([O:25]C)=[C:16]([O:23]C)[CH:17]=4)[NH:12][C:11]=3[CH:10]=[CH:9][C:8]=2[C:6]1=[O:7].Cl.N1C=CC=CC=1.O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH3:1][N:2]([CH3:27])[CH2:3][CH2:4][N:5]1[C:21](=[O:22])[C:20]2[C:19]3[C:18]4[C:13](=[CH:14][C:15]([OH:25])=[C:16]([OH:23])[CH:17]=4)[NH:12][C:11]=3[CH:10]=[CH:9][C:8]=2[C:6]1=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6481893HCID 6481893, compoundHCID 10176127Pyridinium chloride

Product 1

HCID 6481894HCID 6481894, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 210 mg of N-(2-dimethylaminoethyl)-6,7-dimethoxycarbazole-3,4-dicarboximide and 1.66 g of pyridine hydrochloride was sealed in a tube and stirred at 200°-210° C. for 2 hours. Then, 150 ml of water and 100 ml of ethyl acetate were added to the reaction mixture to dissolve the mixture. The solution was adjusted to pH 8.5 with potassium carbonate. 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 mixed with 20 ml of diethyl ether, and the mixture was stirred for 10 minutes. The resulting insoluble material was collected by filtration and recrystallized from n-propanol to obtain 58 mg (yield: 31%) of N-(2-dimethylaminoethyl)-6,7-dihydroxycarbazole-3,4-dicarboximide as yellow crystals.

Workup

  1. customwas sealed in a tube
  2. dissolutionto dissolve the mixture
  3. customThe organic layer was separated
  4. washwashed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous potassium carbonate
  6. customThe solvent was removed by distillation under reduced pressure
  7. additionThe residue was mixed with 20 ml of diethyl ether
  8. stirringthe mixture was stirred for 10 minutes
  9. filtrationThe resulting insoluble material was collected by filtration
  10. customrecrystallized from n-propanol

Sources & evidence

ORD record
ord-b49a08026ca3470e880d946f5cba12ca
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

Loading…