Ethyl 5-nitro-1-benzothiophene-2-carboxylate → Ethyl 5-amino-1-benzothiophene-2-carboxylate

HRID 1172866Notes

Reaction equation

HRID 1172866 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([N+:15]([O-])=O)=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([NH2:15])=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 737499Ethyl 5-nitro-1-benzothiophene-2-carboxylate

Product 1

HCID 2764450Ethyl 5-amino-1-benzothiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 5-nitro-benzo[b]thiophene-2-carboxylic acid ethyl ester (10.52 g, 41.89 mmol) and 10% Pd/C (1.1 g) in 450 mL of EtOH was hydrogenated under 1 atm of H2 for 4 d at rt. The reaction mixture was filtered and the filtrate was concentrated and dried to give 5-amino-benzo[b]thiophene-2-carboxylic acid ethyl ester as a green solid. A parallel reaction was preformed on 10.61 g of 5-nitro-benzo[b]thiophene-2-carboxylic acid ethyl ester in the same manner. 5-amino-benzo[b]thiophene-2-carboxylic acid ethyl ester was obtained. MS (EI): cal'd 222.0 (MH+), exp 222.2 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customdried

Sources & evidence

ORD record
ord-fa8b0c1a61594e479ff9c81e18f83cb4
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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