Ethyl 2-(5-chloro-2-nitroanilino)benzo[b]thiophene-3-carboxylate → Ethyl 2-(2-amino-5-chloroanilino)benzo[b]thiophene-3-carboxylate

HRID 1281769Notes

Reaction equation

HRID 1281769 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:23]([O-])=O)=[C:6]([CH:22]=1)[NH:7][C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[H][H]>[C].[Pd].C(OCC)(=O)C>[NH2:23][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:22][C:6]=1[NH:7][C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 2

HCID 18422161Ethyl 2-(5-chloro-2-nitroanilino)benzo[b]thiophene-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 18422169Ethyl 2-(2-amino-5-chloroanilino)benzo[b]thiophene-3-carboxylate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In the same manner as in Starting Material Synthesis Example 19 and using ethyl 2-(5-chloro-2-nitroanilino)benzo[b]thiophene-3-carboxylate, ethyl acetate, 10% palladium-carbon and hydrogen (60 atm kg/cm2), ethyl 2-(2-amino-5-chloroanilino)benzo[b]thiophene-3-carboxylate is obtained.

Workup

  1. customMaterial Synthesis Example 19

Sources & evidence

ORD record
ord-7374502e6d9c475c969dbb4c71927f0e
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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