5-Methyl-4-nitro-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amide → 5-Methyl-4-amino-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amide

HRID 583774Notes

Reaction equation

HRID 583774 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12]([C:14]3[S:15][C:16]([CH3:22])=[C:17]([N+:19]([O-])=O)[CH:18]=3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1>CO.[Ni]>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12]([C:14]3[S:15][C:16]([CH3:22])=[C:17]([NH2:19])[CH:18]=3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 1

HCID 465857615-Methyl-4-nitro-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amide

Product 1

HCID 611175195-Methyl-4-amino-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amideYield 93.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Sponge nickel (0.7 g water wet) was added to a solution of 5-methyl-4-nitro-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amide (0.72 g, 2.2 mmol) in methanol (50 mL), and the mixture was hydrogenated at room temperature under a hydrogen atmosphere at a starting pressure of 50 psi. After a reaction time of 1.77 hours, the pressure was released, and the mixture was filtered. The slurry was rinsed with methanol, and the filtrate was stripped of solvent under reduced pressure to afford 0.6 g of 5-methyl-4-amino-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amide as an oil.

Workup

  1. customwas hydrogenated at room temperature under a hydrogen atmosphere at a starting pressure of 50 psi
  2. customAfter a reaction time of 1.77 hours
  3. filtrationthe mixture was filtered
  4. washThe slurry was rinsed with methanol

Sources & evidence

ORD record
ord-3a8858b570564cb98baf67f33ec5fb82
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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