Ethanol → HCID 54275090, compound

HRID 1267927Notes

Reaction equation

HRID 1267927 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([CH3:22])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].C(O)C>[Fe].O>[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([CH3:22])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 54373809HCID 54373809, compound

Product 1

HCID 54275090HCID 54275090, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

[1-(3-Methyl-4-nitrophenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (1.744 g), iron powder (1.52 g), ammonium chloride (1.45 g), ethanol (50 ml) and water (50 ml) were heated to reflux temperature under nitrogen for 2 hours. The mixture was cooled and the iron filtered off. Water (200 ml) was added to the residue and the product extracted into ethyl acetate (3×200 ml), dried (MgSO4), and concentrated to give the sub-title compound (1.56 g).

Workup

  1. temperatureto reflux temperature under nitrogen for 2 hours
  2. temperatureThe mixture was cooled
  3. filtrationthe iron filtered off
  4. additionWater (200 ml) was added to the residue
  5. extractionthe product extracted into ethyl acetate (3×200 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-da3fe01198924eed9efe5630b67adb03
Source dataset
uspto-grants-2003_04
Patent number
US06555541B1

Reaction notes

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