HCID 10830922, compound → HCID 69921283, compound

HRID 2186694Notes

Reaction equation

HRID 2186694 reaction equation
[C:1]1(=[O:26])[C:5]2[C:6]3[C:24]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[NH:18][C:7]=3[CH2:8][C:9]3[NH:10][C:11]4[C:16]([C:17]=3[C:4]=2[C:3](=[O:25])[NH:2]1)=[CH:15][CH:14]=[CH:13][CH:12]=4>Cl.O.CCO.C1(C)C=CC=CC=1.[Zn].Cl[Hg]Cl>[C:3]1(=[O:25])[CH:4]2[C:17]3[C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[NH:10][C:9]=3[CH2:8][C:7]3[NH:18][C:19]4[C:24]([C:6]=3[CH:5]2[C:1](=[O:26])[NH:2]1)=[CH:23][CH:22]=[CH:21][CH:20]=4

Participants

8

Reactant 1

HCID 10830922HCID 10830922, compound

Product 1

HCID 69921283HCID 69921283, compound

Reagents, catalysts & solvents 6

HCID 23994ZincCatalystHCID 24085Mercuric ChlorideCatalystHCID 313Hydrochloric AcidSolvent3×HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

1.20 g (18.4 mmol) of Zn granules are washed with 2×3 ml of 2 N HCl, then immediately added to 90 mg (0.33 mmol) of HgCl2 in 1.5 ml of H2O and 1.5 ml of conc. HCl and the mixture is shaken at room temp. for 10 min. The aq. phase is decanted and the zinc amalgam is additionally washed with 2×3 ml of dil. HCl before it is added to a solution of 60.0 mg (0.18 mmol) of 1,2,3,8,9,10-hexahydroindolo[3′,2′:5,6]pyrrolo-[3′,4′:3,4]cyclohepta[b]indole-1,3-dione in 1.5 ml of 5 N HCl, 1.5 ml of EtOH and 1.5 ml of toluene and heated under reflux. After 1 h, as soon as the reaction solution has cooled to room temp. H2O is added and the mixture is extracted with 2×10 ml of CH2Cl2. The org. extracts are dried over Na2SO4, concentrated in vacuo and purified by column chromatography (SiO2; CH2Cl2/ethyl acetate/MeOH 8:2:0.5): colourless wax, yield 14 mg (23%).

Workup

  1. customThe aq. phase is decanted
  2. washthe zinc amalgam is additionally washed with 2×3 ml of dil. HCl before it
  3. temperatureheated
  4. temperatureunder reflux
  5. waitAfter 1 h
  6. extractionthe mixture is extracted with 2×10 ml of CH2Cl2
  7. dry with materialextracts are dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. custompurified by column chromatography (SiO2; CH2Cl2/ethyl acetate/MeOH 8:2:0.5)

Sources & evidence

ORD record
ord-dcb8ddf3173c45aea36fc007d11cf11d
Source dataset
uspto-grants-2002_06
Patent number
US06407102B1

Reaction notes

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