Ammonia → HCID 21216864, compound

HRID 1586598Notes

Reaction equation

HRID 1586598 reaction equation
[CH3:1][N:2]([CH3:35])[CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[C:17]3[NH:19][C:20]4[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][C:25]=4[C:16]=3[C:15]3[C:28](=[O:32])[O:29][C:30](=O)[C:14]=3[C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[C:10]([O:33][CH3:34])[CH:11]=2.[NH3:36]>C(O)C>[CH3:1][N:2]([CH3:35])[CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[C:17]3[NH:19][C:20]4[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][C:25]=4[C:16]=3[C:15]3[C:28](=[O:32])[NH:36][C:30](=[O:29])[C:14]=3[C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[C:10]([O:33][CH3:34])[CH:11]=2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86753910HCID 86753910, compound

Product 1

HCID 21216864HCID 21216864, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

510 mg (1.08 mmol) 12-(3-Dimethylaminopropyl)-6,7,12,13-tetrahydro-3,9-dimethoxy-5,7-dioxoindolo-[2,3-a]furano[3.4-c]carbazole are heated in an autoclave for 24 hours at 140° C. in 40 ml of a saturated solution of ammonia in ethanol. After cooling, the precipitate obtained is filtered off with suction, chromatographed on silica gel with toluene/ethanol (10:1 v/v) and the fraction with the Rf 0.25 in toluene/ethanol (5:1 v/v) is isolated. 12-(3-Dimethylaminopropyl)-6,7,12, 13-tetrahydro-3,9-dimethoxy-5,7-dioxo-5H-indolo[2,3-a]-pyrrolo[3,4-c]carbazole is obtained in the form of yellow crystals which decompose from about 230° C. This compound can also be prepared from the same starting material by reaction with hexamethyldisilazane and methanol in dimethylformamide analogously to the process described in the literature (Tetrahedron Lett., 1990, 31, 5201).

Workup

  1. temperatureAfter cooling
  2. customthe precipitate obtained
  3. filtrationis filtered off with suction
  4. customchromatographed on silica gel with toluene/ethanol (10:1 v/v)
  5. customthe fraction with the Rf 0.25 in toluene/ethanol (5:1 v/v) is isolated

Sources & evidence

ORD record
ord-695829c7ba8b4ff4890b73d0efeebd3a
Source dataset
uspto-grants-1999_08
Patent number
US05945440

Reaction notes

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