Ethanol → 4-Phenylthiophen-2-amine

HRID 215987Notes

Reaction equation

HRID 215987 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-a73fe8223e3b4f90ba905d3133e4161a
Source dataset
uspto-grants-2012_06
Patent number
US08193215B2

Reaction notes

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