Hydrochloric Acid → HCID 18925302, compound

HRID 1289022Notes

Reaction equation

HRID 1289022 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:31]C(C)C)=[CH:5][C:6]2[C:19]3[C:10](=[C:11]4[C:16](=[CH:17][N:18]=3)[C:15]([O:20]CC3C=CC=CC=3)=[C:14]([O:28][CH3:29])[CH:13]=[CH:12]4)[CH:9]=[CH:8][C:7]=2[CH:30]=1.[C:35]1(C)C=CC(S(OC)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[ClH:53].C(=O)([O-])O.[Na+]>CO.C(Cl)(Cl)Cl.CO.C(O)(=O)C>[Cl-:53].[CH3:1][O:2][C:3]1[C:4]([OH:31])=[CH:5][C:6]2[C:19]3[C:10](=[C:11]4[C:16](=[CH:17][N+:18]=3[CH3:35])[C:15]([OH:20])=[C:14]([O:28][CH3:29])[CH:13]=[CH:12]4)[CH:9]=[CH:8][C:7]=2[CH:30]=1

Participants

9

Reactant 5

HCID 313Hydrochloric Acid2×HCID 6645Methyl p-toluenesulfonateHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 18925320HCID 18925320, compound

Product 1

HCID 18925302HCID 18925302, compoundYield 52.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 21584188Chloroform methanolSolvent

Conditions

Temperature
100 °C

Procedure

227 mg (0.5 mmol) of 2,8-dimethoxy-3-isopropoxy-7-benzyloxy-benzo[c]phenanthridine (compound D-3) was admixed with 932 mg (5 mmol) of methyl p-toluenesulfonate and 35 mg (0.25 mmol) of anhydrous potassium carbonate, and the resultant mixture was heated to 140° C. for 3.5 hours. Then the mixture was admixed with 6 ml of acetic acid and 3 ml of concentrated hydrochloric acid, and heated to 100° C. for 3 hours. After that, the reaction mixture was gradually added to ice water to obtain a dilute mixture, which was then neutralized by portionwise adding thereto sodium hydrogen carbonate. The neutralized mixture was extracted with chloroform and a small amount of methanol. The extract was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue thus obtained was refined by a silica gel chromatography, wherein use was made, as eluant, of a chloroform-methanol mixture (4:1). The main fractions were collected and concentrated to give a dark violet solid material, which was compound E-3 having a structure represented by the general formula E. Then, compound E-3 was dissolved in a small amount of methanol, and acidified by gradually adding thereto a dilute aqueous solution of hydrochloric acid in an amount of from 1.5 to 3.0 mol per 1 mol of the compound, so that the color of the solution of the compound was changed into yellow or orange. The solution was concentrated under reduced pressure to remove the solvent and the excess hydrochloric acid. The residue thus obtained was compound A-3, wherein X- =Cl-. The amount of compound A-3 produced was 98 mg (yield: 52.7%).

Workup

  1. customto obtain a dilute mixture, which
  2. additionby portionwise adding
  3. extractionThe neutralized mixture was extracted with chloroform
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained
  8. customThe main fractions were collected
  9. concentrationconcentrated
  10. customto give a dark violet solid material, which
  11. additionby gradually adding
  12. concentrationThe solution was concentrated under reduced pressure
  13. customto remove the solvent
  14. customThe residue thus obtained
  15. customThe amount of compound A-3 produced

Sources & evidence

ORD record
ord-d2b5e8c953f44b8bac576a44e90a275f
Source dataset
uspto-grants-1998_05
Patent number
US05747502

Reaction notes

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