Ammonium Acetate → 1-Amino-5-(3-thienyl)cyclohexen-3-one

HRID 1700518Notes

Reaction equation

HRID 1700518 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]2[CH2:11][C:10](=O)[CH2:9][C:8](=[O:13])[CH2:7]2)=[CH:2]1.C([O-])(=O)C.[NH4+:18]>C(O)C>[NH2:18][C:10]1[CH2:11][CH:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[CH2:7][C:8](=[O:13])[CH:9]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 183173845-(Thiophen-3-yl)cyclohexane-1,3-dione

Product 1

HCID 183175081-Amino-5-(3-thienyl)cyclohexen-3-oneYield 95.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(3-thienyl)cyclohexane-1,3-dione (10.5 g) and ammonium acetate (13.1 g) in ethanol (200 ml) was refluxed for 16 hours. The reaction solution was concentrated under reduced pressure, and to the residue was added water (50 ml). The resulting crystals were filtered, washed with water and toluene, and dried to give 1-amino-5-(3-thienyl)cyclohexen-3-one (10 g) as pale yellow crystals.

Workup

  1. temperaturewas refluxed for 16 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionto the residue was added water (50 ml)
  4. filtrationThe resulting crystals were filtered
  5. washwashed with water and toluene
  6. customdried

Sources & evidence

ORD record
ord-8e9ac23916064446816bbe0e85c6b670
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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