Water → HCID 68680161, compound

HRID 1443154Notes

Reaction equation

HRID 1443154 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15].O.C(OCC)(=O)C>C(O)(=O)C.[Fe]>[N+:14]([C:6]1[C:5]2[C:10]([CH:9]=[CH:8][CH:7]=1)=[N:11][C:3](=[O:2])[CH:4]=2)([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 13134408HCID 13134408, compound

Product 1

HCID 68680161HCID 68680161, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

4.43 g (18.45 mmol) of methyl-(2,6-dinitrophenyl)-acetate is added in 38.8 ml of glacial acetic acid and 11 ml of water and mixed with 3.75 g of iron powder and stirred for four more hours. In this case, heating to 40 to 60° C. takes place. The reaction mixture is added to ice water, mixed with ethyl acetate and stirred vigorously for ten minutes. The mixture is filtered through a glass fiber filter, the organic phase is separated, and the aqueous phase is extracted twice more with ethyl acetate. The combined organic extracts are washed with brine, dried, and the solvent is spun off after the desiccant is filtered off. The residue is chromatographed on silica gel (mobile solvent:methanol/dichloromethane). 2.38 g of 4-nitro-indol-2-one is isolated. The nitro compound is mixed again in glacial acetic acid/water with 2.7 g of iron powder, and the above-described cycle is passed through another time. 1.63 g of the desired amine is isolated.

Workup

  1. stirringstirred vigorously for ten minutes
  2. filtrationThe mixture is filtered through a glass fiber
  3. filtrationfilter
  4. customthe organic phase is separated
  5. extractionthe aqueous phase is extracted twice more with ethyl acetate
  6. washThe combined organic extracts are washed with brine
  7. customdried
  8. filtrationis filtered off
  9. customThe residue is chromatographed on silica gel (mobile solvent:methanol/dichloromethane)

Sources & evidence

ORD record
ord-86202d8901c140e1bfb3c021506284bf
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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