Ethanol → 4-Phenylthiophen-2-amine

HRID 2104100Notes

Reaction equation

HRID 2104100 reaction equation
C(OC([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][S:8][C:7]=1[NH2:17])=O)C.C(O)C>[OH-].[K+].O>[C:11]1([C:10]2[CH:6]=[C:7]([NH2:17])[S:8][CH:9]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 73242Ethyl 2-amino-4-phenylthiophene-3-carboxylate

Product 1

HCID 125259964-Phenylthiophen-2-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

2-Amino-4-phenyl-thiophene-3-carboxylic acid ethyl ester (5 g, 20.2 mmol) was suspended in 20% potassium hydroxide solution (100 ml) and heated to reflux. Ethanol (100 ml) was added to aid dissolution. The reaction was stirred overnight and then cooled to room temperature and diluted with water (250 ml). The precipitated solid was collected by filtration and dissolved in DCM/ethyl acetate before drying over magnesium sulfate. The solvent was removed in vacuo to give 4-phenyl-thiophen-2-ylamine. Yield 1.05 g (30%).

Workup

  1. temperatureheated to reflux
  2. filtrationThe precipitated solid was collected by filtration
  3. dissolutiondissolved in DCM/ethyl acetate
  4. dry with materialbefore drying over magnesium sulfate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8255025ad8854fa494cff52e640c1792
Source dataset
uspto-grants-2009_08
Patent number
US07576212B2

Reaction notes

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