Ammonium Acetate → 3-Amino-5-(5-methyl-2-thienyl)cyclohex-2-en-1-one

HRID 1700494Notes

Reaction equation

HRID 1700494 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH:7]2[CH2:12][C:11](=O)[CH2:10][C:9](=[O:14])[CH2:8]2)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:19]>C(O)C>[NH2:19][C:11]1[CH2:12][CH:7]([C:5]2[S:6][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH2:8][C:9](=[O:14])[CH:10]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 183174245-(5-Methylthiophen-2-yl)cyclohexane-1,3-dione

Product 1

HCID 183174203-Amino-5-(5-methyl-2-thienyl)cyclohex-2-en-1-oneYield 81.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(5-methyl-2-thienyl)cyclohexane-1,3-dione (4.16 g) and ammonium acetate (4.6 g) in ethanol (50 ml) was refluxed for 15 hours, and the reaction solution was concentrated under reduced pressure. To the residue was added water (60 ml), and the resulting crystals were filtered. The crystals were washed with water and toluene, and dried to give 1-amino-5-(5-methyl-2-thienyl)cyclohexen-3-one (3.37 g) as pale yellow crystals.

Workup

  1. temperaturewas refluxed for 15 hours
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additionTo the residue was added water (60 ml)
  4. filtrationthe resulting crystals were filtered
  5. washThe crystals were washed with water and toluene
  6. customdried

Sources & evidence

ORD record
ord-cd4dc47f45dc45c9a2d5a9026be1bbed
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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