Ethyl Acetate → HCID 18368061, compound

HRID 379858Notes

Reaction equation

HRID 379858 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])=[C:6]2[N+:18]([O-])=O.[Cl-].[NH4+].C(OCC)(=O)C>C(O)C.[Fe]>[NH2:18][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:8][C:7]=1[C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 18367837HCID 18367837, compound

Product 1

HCID 18368061HCID 18368061, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-methoxy-2-(N-methoxy-N-methylamino)carbonyl-3-nitroindole (step 2, 110 mg, 0.39 mmol), ammonium chloride (11 mg, 0.20 mmol) and iron powder (115 mg, 1.97 mmol) in 70% aqueous ethanol (10 ml) was heated at reflux for 2 h, and then cooled and filtered through a pad of Celite. The pad was washed copiously with a mixture of ethanol/ethyl acetate (1:1 v/v) and the combined washing evaporated. The residue was diluted with ethyl acetate (50 ml), washed with saturated aqueous sodim bicarbonate (30 ml) and dried (Na2SO4). Removal of solvent gave product as an oil. tlc: Rf=0.5 (50% ethyl acetate in hexanes)

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. filtrationfiltered through a pad of Celite
  5. washThe pad was washed copiously with a mixture of ethanol/ethyl acetate (1:1 v/v)
  6. washthe combined washing
  7. customevaporated
  8. additionThe residue was diluted with ethyl acetate (50 ml)
  9. washwashed with saturated aqueous sodim bicarbonate (30 ml)
  10. dry with materialdried (Na2SO4)
  11. customRemoval of solvent
  12. customgave product as an oil

Sources & evidence

ORD record
ord-66ffb81e50f7467da15a4f0e074a5a4a
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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