Sodium Dithionite → HCID 21938263, compound

HRID 1242133Notes

Reaction equation

HRID 1242133 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[CH2:14][C:15](=O)[CH2:16][CH2:17][CH3:18])([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O1CCCC1.CO.O>[CH3:11][O:10][C:8]([C:7]1[CH:6]=[C:5]2[C:4](=[CH:13][CH:12]=1)[NH:1][C:15]([CH2:16][CH2:17][CH3:18])=[CH:14]2)=[O:9]

Participants

6

Reactant 2

HCID 24489Sodium DithioniteHCID 21938317HCID 21938317, compound

Product 1

HCID 21938263HCID 21938263, compoundYield 71.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-nitro-3-(2-oxopentyl)benzoate (5.42 g) is dissolved in a mixed solvent of tetrahydrofuran (20 ml) and methanol (20 ml), to which is added a suspension of sodium hydrosulfite (52.2 g) in water (60 ml). After having been refluxed for 2 hours, this is subjected to liquid-liquid separation by adding ethyl acetate (300 ml) and water (200 ml) thereto. The organic layer is washed with a saline solution, dried and concentrated. The resulting residue is purified through silica gel column chromatography to obtain 5-(methoxycarbonyl)-2-propylindole (3.16 g).

Workup

  1. additionis added
  2. temperatureAfter having been refluxed for 2 hours
  3. customthis is subjected to liquid-liquid separation
  4. additionby adding ethyl acetate (300 ml) and water (200 ml)
  5. washThe organic layer is washed with a saline solution
  6. customdried
  7. concentrationconcentrated
  8. customThe resulting residue is purified through silica gel column chromatography

Sources & evidence

ORD record
ord-1fc091c782394dc2acb2ed1260ae805b
Source dataset
uspto-grants-2006_10
Patent number
US07115647B2

Reaction notes

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