Ethyl 2-(5-fluoro-2-nitroanilino)-6-methylbenzo[b]thiophene-3-carboxylate → Ethyl 2-(2-amino-5-fluoroanilino)-6-methylbenzo[b]thiophene-3-carboxylate

HRID 1281775Notes

Reaction equation

HRID 1281775 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:24]([O-])=O)=[C:6]([CH:23]=1)[NH:7][C:8]1[S:12][C:11]2[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:10]=2[C:9]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[H][H]>[C].[Pd].C(OCC)(=O)C>[NH2:24][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:23][C:6]=1[NH:7][C:8]1[S:12][C:11]2[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:10]=2[C:9]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 2

HCID 18422188Ethyl 2-(5-fluoro-2-nitroanilino)-6-methylbenzo[b]thiophene-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 18422258Ethyl 2-(2-amino-5-fluoroanilino)-6-methylbenzo[b]thiophene-3-carboxylateYield 88.1%

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-fluoro-2-nitroanilino)-6-methylbenzo[b]thiophene-3-carboxylate (1.9 g), ethyl acetate (200 ml), 10% palladium-carbon (0.4 g) and hydrogen (60 atm kg/cm2), ethyl 2-(2-amino-5-fluoroanilino)-6-methylbenzo[b]thiophene-3-carboxylate (1.54 g) was obtained.

Workup

  1. customMaterial Synthesis Example 19

Sources & evidence

ORD record
ord-7b84c3f58fc044c08c2bb7bf90c7d641
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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