Hydrochloric Acid → HCID 86753909, compound

HRID 1586596Notes

Reaction equation

HRID 1586596 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

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

Sources & evidence

ORD record
ord-f5573b0aa59742d1914a450a9c81b6ef
Source dataset
uspto-grants-1999_08
Patent number
US05945440

Reaction notes

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