2,5-Dichloro-4-nitro-thiophene-3-carboxylic acid methylamide → 4-Amino-2,5-dichloro-thiophene-3-carboxylic acid methylamide

HRID 1688085Notes

Reaction equation

HRID 1688085 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:9]([N+:10]([O-])=O)=[C:8]([Cl:13])[S:7][C:6]=1[Cl:14])=[O:4].[H][H]>C(O)C.[Ni]>[CH3:1][NH:2][C:3]([C:5]1[C:9]([NH2:10])=[C:8]([Cl:13])[S:7][C:6]=1[Cl:14])=[O:4]

Participants

5

Reactant 2

HCID 672643122,5-Dichloro-4-nitro-thiophene-3-carboxylic acid methylamideHCID 178418361HCID 178418361, compound

Product 1

HCID 672645864-Amino-2,5-dichloro-thiophene-3-carboxylic acid methylamideYield 102.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2,5-dichloro-4-nitro-thiophene-3-carboxylic acid methylamide (565 mg) and Raney Ni (50 mg) in ethanol was stirred under 1 atm hydrogen for 5 hours. The reaction mixture was filtered and concentrated to afford 510 mg of 4-amino-2,5-dichloro-thiophene-3-carboxylic acid methylamide: 1H NMR (300 MHz, CDCl3) δ 3.8-3.6 (bs, 3H), 3.0 (d, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-101049a27564443f9776ca97c1478c75
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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