Ethyl 2-(2,3-dichloro-6-nitroanilino)benzo[b]thiophene-3-carboxylate → Ethyl 2-(6-amino-2,3-dichloroanilino)benzo[b]thiophene-3-carboxylate

HRID 649928Notes

Reaction equation

HRID 649928 reaction equation
[Cl:1][C:2]1[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]([N+:24]([O-])=O)[C:3]=1[NH:4][C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[C:6]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[H][H]>[C].[Pd].C(OCC)(=O)C>[NH2:24][C:19]1[C:3]([NH:4][C:5]2[S:9][C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[C:6]=2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:2]([Cl:1])[C:22]([Cl:23])=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 18422195Ethyl 2-(2,3-dichloro-6-nitroanilino)benzo[b]thiophene-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 18422327Ethyl 2-(6-amino-2,3-dichloroanilino)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-(2,3-dichloro-6-nitroanilino)benzo[b]thiophene-3-carboxylate, ethyl acetate, 10% palladium-carbon and hydrogen (60 atm kg/cm2), ethyl 2-(6-amino-2,3-dichloroanilino)benzo[b]thiophene-3-carboxylate is obtained.

Workup

  1. customMaterial Synthesis Example 19

Sources & evidence

ORD record
ord-45aaf45febc84d218e4bd2895a98330f
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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