Acetic Acid → 2-Methoxy-11-(2-nitroethyl)-6h-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindole

HRID 2298757Notes

Reaction equation

HRID 2298757 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]3[CH2:11][C:12]4[C:17]([C:9]3=[C:8]([CH:18]=[CH:19][N+:20]([O-:22])=[O:21])[C:7]=2[N:23]=1)=[CH:16][CH:15]=[CH:14][CH:13]=4.C(Cl)(Cl)Cl.[BH4-].[Na+].C(O)(=O)C>C(O)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]3[CH2:11][C:12]4[C:17]([C:9]3=[C:8]([CH2:18][CH2:19][N+:20]([O-:22])=[O:21])[C:7]=2[N:23]=1)=[CH:16][CH:15]=[CH:14][CH:13]=4

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 699693982-Methoxy-11-[2-nitroethenyl]-6h-pyrido[2',3':4,5]pyrrolo[2,1-a]-isoindole

Product 1

HCID 183787062-Methoxy-11-(2-nitroethyl)-6h-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Under argon and in an anhydrous medium, 660 mg (2.15 mmol) of the compound obtained in Step F are suspended in 10 ml of isopropanol and 30 ml of chloroform in the presence of 1.5 g of 230-400 mesh silica; 408 mg (10.75 mmol) of sodium borohydride are added slowly. After 30 minutes' stirring at room temperature, acetic acid is added and the reaction mixture is filtered through a glass frit. After removal of the solvents by evaporation, the residue is diluted in dichloromethane and washed with water. The organic phase is then dried over magnesium sulphate, filtered and concentrated to yield the title compound in the form of a yellow solid.

Workup

  1. filtrationthe reaction mixture is filtered through a glass frit
  2. customAfter removal of the solvents
  3. customby evaporation
  4. additionthe residue is diluted in dichloromethane
  5. washwashed with water
  6. dry with materialThe organic phase is then dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5b6d7d1acce8400aab6e007a62648644
Source dataset
uspto-grants-2002_12
Patent number
US06495543B1

Reaction notes

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