HCID 7131469, compound → HCID 15907305, compound

HRID 1357440Notes

Reaction equation

HRID 1357440 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=1

Participants

4

Reactant 1

HCID 7131469HCID 7131469, compound

Product 1

HCID 15907305HCID 15907305, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3 g (13.5 mmol) of 4-nitro-2-(2-thienyl)phenol are dissolved in 40 ml ethanol and hydrogenated at 25° C. after addition of 600 mg of a palladium activated carbon catalyst (10%). The catalyst is removed by filtration after up-take of the theoretically required amount of hydrogen. After concentrating the solution in a rotary evaporator the reaction mixture is poured into 20 ml of cold diethyl ether. The precipitated product is separated from the solution by filtration and dried. 1.95 g (75% of theoretical yield) of 4-amino-2-(2-thienyl)phenol are obtained with a melting point of 130 to 132° C.

Workup

  1. customThe catalyst is removed by filtration after up-take of the theoretically required amount of hydrogen
  2. concentrationAfter concentrating the solution
  3. customin a rotary evaporator the reaction mixture
  4. additionis poured into 20 ml of cold diethyl ether
  5. customThe precipitated product is separated from the solution by filtration
  6. customdried

Sources & evidence

ORD record
ord-e998e0b06658462cafe8f65ef352ec2c
Source dataset
uspto-grants-2003_07
Patent number
US06592631B2

Reaction notes

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