Ethyl 2-(4-methyl-2-nitroanilino)benzo[b]thiophene-3-carboxylate → Ethyl 2-(2-amino-4-methylanilino)benzo[b]thiophene-3-carboxylate

HRID 649912Notes

Reaction equation

HRID 649912 reaction equation
[CH3:1][C:2]1[CH:22]=[CH:21][C:5]([NH:6][C:7]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]=2[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:4]([N+:23]([O-])=O)[CH:3]=1.[H][H]>[C].[Pd].C(OCC)(=O)C>[NH2:23][C:4]1[CH:3]=[C:2]([CH3:1])[CH:22]=[CH:21][C:5]=1[NH:6][C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[C:8]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 2

HCID 18422341Ethyl 2-(4-methyl-2-nitroanilino)benzo[b]thiophene-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 18422219Ethyl 2-(2-amino-4-methylanilino)benzo[b]thiophene-3-carboxylateYield 62.2%

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-(4-methyl-2-nitroanilino)benzo[b]thiophene-3-carboxylate (6.5 g), ethyl acetate (140 ml), 10% palladium-carbon and hydrogen (500 mg, 60 atm kg/cm2), ethyl 2-(2-amino-4-methylanilino)benzo[b]thiophene-3-carboxylate (3.7 g) was obtained.

Workup

  1. customMaterial Synthesis Example 19

Sources & evidence

ORD record
ord-deb4705a39df4b1ca8f577a5b398c156
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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