3-methyl-5-nitro-1-benzothiophene → HCID 20824576, compound

HRID 1766285Notes

Reaction equation

HRID 1766285 reaction equation
[CH3:1][C:2]1[C:3]2[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1>CO.[Pd]>[CH3:1][C:2]1[C:3]2[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1

Participants

4

Reactant 1

HCID 2686253-methyl-5-nitro-1-benzothiophene

Product 1

HCID 20824576HCID 20824576, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-methyl-5-nitro-benzo[b]thiophene [18] (95 mg, 0.492 mmol) in methanol (20 mL) was added 5% palladium on carbon (20 mg) and the mixture was stirred under 1 atm H2 for 8.5h. The mixture was filtered through celite and the filtrate evaporated. The residue was passed through a silica plug to afford 3-methyl-benzo[b]thiophen-5-ylamine as a dark orange solid (31 mg, 39%), single spot at Rf 0.31 (4:1 hexane:ethyl acetate). 1H NMR (CDCl3): δ 7.60 (1H, d, J=8.4 Hz), 7.02 (1H, s), 7.00 (1H, d, J=2.2 Hz), 6.79 (1H, dd, J=8.4, 2.2 Hz), 2.37 (3H, s).

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-b9d4928ef6074456bfc8c703fa023de4
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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