Potassium Carbonate → 12-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-6,7,12,13-tetrahydro-6-methyl-5,7-dioxo-5H-indolo[2,3-a]pyrrolo-[3,4-c]carbazole

HRID 1586602Notes

Reaction equation

HRID 1586602 reaction equation
[C:1]([CH2:3][CH2:4][N:5]1[C:17]2[C:16]3[NH:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=4[C:15]=3[C:14]3[C:25](=[O:30])[N:26]([CH3:29])[C:27](=[O:28])[C:13]=3[C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)#N.[OH-].[K+].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[CH3:57][C:58]1([CH3:75])[O:62]C(COS(C2C=CC(C)=CC=2)(=O)=O)C[O:59]1.C(OC(C)C)(C)C.CC(C)=O>C1(C)C=CC=CC=1>[CH3:57][C:58]1([CH3:75])[O:62][CH:3]([CH2:4][N:5]2[C:17]3[C:16]4[NH:18][C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=5[C:15]=4[C:14]4[C:25](=[O:30])[N:26]([CH3:29])[C:27](=[O:28])[C:13]=4[C:12]=3[C:11]3[C:6]2=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:1][O:59]1

Participants

8

Reactant 6

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 2350972,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonateHCID 2121684212-(2-Cyanoethyl)-6,7,12,13-tetrahydro-6-methyl-5,7-dioxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazoleHCID 22221350Acetone diisopropyl ether

Product 1

HCID 2121686012-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-6,7,12,13-tetrahydro-6-methyl-5,7-dioxo-5H-indolo[2,3-a]pyrrolo-[3,4-c]carbazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3 g (8.84 mmol) 6,7,12,13-Tetrahydro-6-methyl-5,1-dioxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole (precursor for Example 5) are stirred for 2 hours at 20° C. with 595 mg (9 mmol) powdered potassium hydroxide, 620 mg (4.5 mmol) potassium carbonate and 300 mg (1.1 mmol) 18-crown-6 in 200 ml toluene under an atmosphere of nitrogen. Subsequently, 2.6 g (9 mmol) 2,2-dimethyl-4-(4-methylphenylsulphonyloxymethyl)-1,3-dioxolan (see Biochemistry, 1971, 10, 3204) are added thereto and the reaction mixture is heated under reflux for 16 hours. After cooling, the reaction mixture is evaporated in a vacuum and the residue is taken up in ethyl acetate and water. The ethyl acetate solution is separated off, washed with water, dried over anhydrous sodium sulphate, filtered and evaporated. The residue is chromatographed on silica gel with toluene/acetone (9:1 v/v), the fraction with the Rf 0.65 in toluene/acetone (3:1 v/v) is isolated, stirred with 20 ml diisopropyl ether/acetone (4:1 v/v) and the yellow crystals formed of 12-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-6,7,12,13-tetrahydro-6-methyl-5,7-dioxo-5H-indolo[2,3-a]pyrrolo-[3,4-c]carbazole filtered off.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 16 hours
  3. temperatureAfter cooling
  4. customthe reaction mixture is evaporated in a vacuum
  5. customThe ethyl acetate solution is separated off
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is chromatographed on silica gel with toluene/acetone (9:1 v/v)
  11. customthe fraction with the Rf 0.65 in toluene/acetone (3:1 v/v) is isolated

Sources & evidence

ORD record
ord-61f9af637fe1436ab5db653e407a42dc
Source dataset
uspto-grants-1999_08
Patent number
US05945440

Reaction notes

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