Hydrochloric Acid → HCID 86753909, compound

HRID 1418634Notes

Reaction equation

HRID 1418634 reaction equation
[CH2:1]([N:3]([CH2:34][CH3:35])[CH2:4][CH:5]([OH:33])[CH2:6][N:7]1[C:19]2[C:18]3[NH:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[C:17]=3[C:16]3[C:27](=[O:32])N(C)[C:29](=[O:30])[C:15]=3[C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:2].Cl.[OH-:37].[K+]>>[CH2:34]([N:3]([CH2:1][CH3:2])[CH2:4][CH:5]([OH:33])[CH2:6][N:7]1[C:19]2[C:18]3[NH:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[C:17]=3[C:16]3[C:27](=[O:37])[O:32][C:29](=[O:30])[C:15]=3[C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:35]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 21216869HCID 21216869, compound

Product 1

HCID 86753909HCID 86753909, compound

Procedure

The starting material is prepared in the following manner: 440 mg (0.94 mmol) (±)-12-(3-diethylamino-2-hydroxy-1-propyl)-6,7,12,13-tetrahydro-6-methyl-5,7-dioxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole are heated under reflux for 1.5 hours in 100 ml 10% methanolic potassium hydroxide solution. After cooling the reaction mixture is acidified with semi-concentrated hydrochloric acid, filtered and the filtrate evaporated. The residue is taken up in 10% potassium carbonate solution and ethyl acetate and the organic phase is washed with water and dried over anhydrous sodium sulphate. It is filtered, evaporated and the residue is stirred with 25 ml diisopropyl ether and the crystals formed are filtered off. (±)-12-(3-Diethylamino-2-hydroxy-1-propyl)-6,7,12,13-tetrahydro-5,7-dioxoindolo-[2,3-a]furano[3,4-c]carbazole is obtained in the form of yellow crystals which decompose from about 200° C.

Workup

  1. customThe starting material is prepared in the following manner
  2. temperatureAfter cooling the reaction mixture
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. washethyl acetate and the organic phase is washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationIt is filtered
  8. customevaporated
  9. customthe crystals formed
  10. filtrationare filtered off

Sources & evidence

ORD record
ord-7ece698d30b74a72be4d11131eee7ca6
Source dataset
uspto-grants-1999_03
Patent number
US05883114

Reaction notes

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