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

HRID 1764246Notes

Reaction equation

HRID 1764246 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:7]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-])=O)=[O:5])[CH3:2]>C(O)C.[Pd]>[NH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[NH:13][C:7]1[S:8][C:9]([CH2:11][CH3:12])=[CH:10][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

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-e9cd27e1527f4923888fec17d087e5de
Source dataset
uspto-grants-1978_09
Patent number
US04115568

Reaction notes

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