Hydrochloric Acid → HCID 86755876, compound

HRID 365403Notes

Reaction equation

HRID 365403 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[C@H:13]1[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12]1)[N:7]=[C:6]2[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=1.Cl.O>CO.[Fe]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[C@H:13]1[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12]1)[N:7]=[C:6]2[C:19]1[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86755877HCID 86755877, compound

Product 1

HCID 86755876HCID 86755876, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

8.5 g of (+/-)-cis-8,9-dimethoxy-6-(4-nitrophenyl)-1,2,3,4,4a,10b-hexahydrophenanthridine are dissolved in 200 ml of methanol, and the solution is treated with 5 ml of concentrated hydrochloric acid, 20 ml of water and 800 mg of iron powder and stirred overnight at RT. The reaction mixture is filtered, the filtrate is concentrated, the residue is extracted with sodium hydrogencarbonate solution/ethyl acetate, and the organic phase is dried using sodium sulfate and concentrated. The residue is chromatographed on silica gel using a mixture of toluene/dioxane/triethylamine in the ratio 40:20:2. After concentration of the corresponding eluate fractions, 5.5 g (70.5% of theory) of the title compound of m.p. 159.5-161° C. are obtained.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. extractionthe residue is extracted with sodium hydrogencarbonate solution/ethyl acetate
  4. customthe organic phase is dried
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel using
  7. additiona mixture of toluene/dioxane/triethylamine in the ratio 40:20:2

Sources & evidence

ORD record
ord-6895fa458b574598b57bfeb2c250ff46
Source dataset
uspto-grants-2000_10
Patent number
US06127378

Reaction notes

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