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

HRID 1766282Notes

Reaction equation

HRID 1766282 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([N+:14]([O-])=O)=[CH:13][C:7]=2[CH:6]=1)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([NH2:14])=[CH:13][C:7]=2[CH:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 1489057Methyl 5-nitro-1-benzothiophene-2-carboxylate

Product 1

HCID 2824064Methyl 5-amino-1-benzothiophene-2-carboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-nitro-benzo[b]thiophene-2-carboxylic acid methyl ester [15] (130 mg, 0.548 mmol) in methanol (30 mL) was added 5% palladium on carbon (20 mg) and the mixture was stirred under 1 atm H2 for 2 h. The mixture was filtered through celite and the filtrate evaporated. The residue was passed through a silica column to afford 5-amino-benzo[b]thiophene-2-carboxylic acid methyl ester as a pale yellow solid (94 mg, 83%), single spot at Rf 0.75 (95:5 dichloromethane:methanol). 1H NMR (CDCl3): δ 7.86 (1H, s), 7.61 (1H, d, J=8.7 Hz), 7.11 (1H, d, J=2.2 Hz), 6.88(1H, dd, J=8.7, 2.5 Hz), 3.91 (3H, s), 3.76 (2H, s, N—H2) [16].

Workup

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

Sources & evidence

ORD record
ord-908cee6b4bd041d4936f0091b1ca6dc8
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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