Ethyl 5-ethyl-2-(2-nitroanilino)-thiophene-3-carboxylate → Ethyl 2-(2-aminoanilino)-5-ethyl-thiophene-3-carboxylate

HRID 1764283Notes

Reaction equation

HRID 1764283 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)=[C:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:4]=1)[CH3:2]>C(O)C.[Pd]>[NH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:6]1[S:7][C:3]([CH2:1][CH3:2])=[CH:4][C:5]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

4

Reactant 1

HCID 12442327Ethyl 5-ethyl-2-(2-nitroanilino)-thiophene-3-carboxylate

Product 1

HCID 12442333Ethyl 2-(2-aminoanilino)-5-ethyl-thiophene-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 5-ethyl-2-(2-nitroanilino)-thiophene-3-carboxylate (20.7 g) in ethanol (150 ml) was catalytically reduced over 10% palladium on charcoal (2.0 g) at 60 p.s.i. The catalyst was removed by filtration and the solvent removed by distillation in vacuo. The title product so obtained had a melting point of 50°-52° C. (hexane).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent removed by distillation in vacuo

Sources & evidence

ORD record
ord-932fde9c1e6a4a9888f3a6e8d87de4d9
Source dataset
uspto-grants-1978_09
Patent number
US04115574

Reaction notes

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