Potassium Bicarbonate → HCID 21216867, compound

HRID 1418638Notes

Reaction equation

HRID 1418638 reaction equation
CC1(C)[O:6][CH:5]([CH2:7][N:8]2[C:20]3[C:19]4[NH:21][C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=5[C:18]=4[C:17]4[C:28](=[O:32])[NH:29][C:30](=[O:31])[C:16]=4[C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:4][O:3]1.C(=O)([O-])O.[K+]>Cl.C(O)C>[OH:6][CH:5]([CH2:4][OH:3])[CH2:7][N:8]1[C:20]2[C:19]3[NH:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=4[C:18]=3[C:17]3[C:28](=[O:32])[NH:29][C:30](=[O:31])[C:16]=3[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2

Participants

4

Reactant 2

HCID 516893Potassium BicarbonateHCID 21216890HCID 21216890, compound

Product 1

HCID 21216867HCID 21216867, compound

Reagents, catalysts & solvents 1

HCID 21887872Ethanol hydrochlorideSolvent

Procedure

150 mg (0.34 mmol) 12-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-6,7,12,13-tetrahydro-5,7-dioxo-5H-indolo-[2,3-a]pyrrolo[3,4-c]carbazole in 50 ml 1N hydrochloric acid/ethanol (1:1 v/v) are stirred for 16 hours at 60° C. After cooling, the reaction mixture is neutralised with 10% potassium hydrogen carbonate solution and extracted twice with, in each case, 100 ml ethyl acetate. The ethyl acetate extracts are washed with 100 ml of water, dried over anhydrous sodium sulphate, filtered and evaporated. The residue is chromatographed on silica gel with toluene/acetone (4:1 v/v) and the fraction with the Rf 0.2 in toluene/acetone (3:1 v/v) is isolated. 12-(2,3-Dihydroxy-1-propyl)-6,7,12,13-tetrahydro-5,7-dioxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole is obtained in the form of an orange amorphous powder which decomposes from about 310° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted twice with, in each case, 100 ml ethyl acetate
  3. washThe ethyl acetate extracts are washed with 100 ml of water
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is chromatographed on silica gel with toluene/acetone (4:1 v/v)
  8. customthe fraction with the Rf 0.2 in toluene/acetone (3:1 v/v) is isolated

Sources & evidence

ORD record
ord-6a8d042079e64ba0b5ac047be8c08664
Source dataset
uspto-grants-1999_03
Patent number
US05883114

Reaction notes

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