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

HRID 1281767Notes

Reaction equation

HRID 1281767 reaction equation
[F: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(OCC)(=O)C.[C].[Pd]>[NH2:23][C:5]1[CH:4]=[CH:3][C:2]([F: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 18422317Ethyl 2-(5-fluoro-2-nitroanilino)benzo[b]thiophene-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 18422159Ethyl 2-(2-amino-5-fluoroanilino)benzo[b]thiophene-3-carboxylateYield 52.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2-(5-fluoro-2-nitroanilino)benzo[b]thiophene-3-carboxylate (50.7 g) was dissolved in ethyl acetate (1000 ml) and 10% palladium-carbon (8.0 g) was added. The mixture was stirred with hydrogen (60 kg/cm2) at 55° C. for 5 hr. The reaction mixture was cooled and the catalyst was filtered off. The filtrate was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform) to give ethyl 2-(2-amino-5-fluoroanilino)benzo[b]thiophene-3-carboxylate (24.5 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe catalyst was filtered off
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-abbbe6be5c2544dba8439acd6cc7da9f
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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