Ethyl Acetate → 4-(2-Amino-4-chloroanilino)thiophene-3-carbonitrile

HRID 1764289Notes

Reaction equation

HRID 1764289 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([NH:6][C:7]2[C:11]([C:12]#[N:13])=[CH:10][S:9][CH:8]=2)=[C:4]([N+:16]([O-])=O)[CH:3]=1.C(OCC)(=O)C>C(O)C.[Pd]>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([NH:6][C:7]2[C:11]([C:12]#[N:13])=[CH:10][S:9][CH:8]=2)=[C:4]([NH2:16])[CH:3]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 12658710HCID 12658710, compound

Product 1

HCID 203877584-(2-Amino-4-chloroanilino)thiophene-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(4-Chloro-2-nitroanilino)-thiophene-4-nitrile (17.18 g, 0.06 mol) was hydrogenated in ethanol (300 ml) and ethyl acetate (100 ml) using a palladium/charcoal catalyst (3.5 g, 10%) in a Parr hydrogenator to give 3-(4-Chloro-2-aminoanilino)-thiophene-4-nitrile. After two hours, the reaction was complete, the catalyst was filtered off and the solution was evaporated to dryness under vacuum.

Sources & evidence

ORD record
ord-863802e8945343dfbf8c4490d64a4e00
Source dataset
uspto-grants-1978_09
Patent number
US04115574

Reaction notes

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