[1-(2-Ethoxy-2-oxoethyl)-3-nitro-1H-indol-4-yl]acetic Acid → Ethyl (4-oxo-4,5-dihydropyrrolo[2,3,4-if]isoquinolin-1(3H)-yl)acetate

HRID 2426202Notes

Reaction equation

HRID 2426202 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([CH2:15][C:16](O)=[O:17])[CH:11]=[CH:12][CH:13]=2)[C:8]([N+:19]([O-])=O)=[CH:7]1)[CH3:2]>CC(O)=O.O.[Fe]>[O:17]=[C:16]1[CH2:15][C:10]2[C:9]3=[C:14]([N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:22])[CH:7]=[C:8]3[NH:19]1)[CH:13]=[CH:12][CH:11]=2

Participants

5

Reactant 1

HCID 57426202[1-(2-Ethoxy-2-oxoethyl)-3-nitro-1H-indol-4-yl]acetic Acid

Product 1

HCID 59257910Ethyl (4-oxo-4,5-dihydropyrrolo[2,3,4-if]isoquinolin-1(3H)-yl)acetate

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of [1-(2-ethoxy-2-oxoethyl)-3-nitro-1H-indol-4-yl]acetic acid from Step F (250 mg, 0.816 mmol) in AcOH (18 mL) and H2O (2 mL) was added iron powder (456 mg, 8.16 mmol) and the reaction mixture was heated at 80° C. for 18 h. The mixture was concentrated in vacuo to remove most of the solvent and the residue was partitioned between saturated aqueous NaHCO3 (5 mL) and EtOAc (25 mL). The organic layer was washed with brine, then dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound, which was of sufficient purity for use in the next step. MS: m/z=259 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto remove most of the solvent
  3. customthe residue was partitioned between saturated aqueous NaHCO3 (5 mL) and EtOAc (25 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa2e8b79813243de8e7e9ef61004d456
Source dataset
uspto-grants-2011_06
Patent number
US07968540B2

Reaction notes

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