5-Methyl-4-nitro-thiophene-2-carboxylic acid benzyl ester → 5-Methyl-4-amino-thiophene-2-carboxylic acid benzyl ester

HRID 583761Notes

Reaction equation

HRID 583761 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[S:12][C:13]([CH3:19])=[C:14]([N+:16]([O-])=O)[CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1.[Ni]>[CH2:1]([O:8][C:9]([C:11]1[S:12][C:13]([CH3:19])=[C:14]([NH2:16])[CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 381853005-Methyl-4-nitro-thiophene-2-carboxylic acid benzyl ester

Product 1

HCID 613104205-Methyl-4-amino-thiophene-2-carboxylic acid benzyl esterYield 107%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Sponge nickel (0.6 g water wet) was added to a solution of 5-methyl-4-nitro-thiophene-2-carboxylic acid benzyl ester (0.93 g, 3.4 mmol), prepared as described in Step 1 above, in tetrahydrofuran (50 mL), and the mixture was hydrogenated at room temperature under hydrogen atmosphere at a starting pressure of 50 psi. After a reaction time of 2.4 hours, the pressure was released and the mixture filtered. The slurry was rinsed with tetrahydrofuran, and the filtrate was stripped of solvent under reduced pressure, leaving 0.9 g of 5-methyl-4-amino-thiophene-2-carboxylic acid benzyl ester as an oil.

Workup

  1. customprepared
  2. customwas hydrogenated at room temperature under hydrogen atmosphere at a starting pressure of 50 psi
  3. customAfter a reaction time of 2.4 hours
  4. filtrationthe mixture filtered
  5. washThe slurry was rinsed with tetrahydrofuran

Sources & evidence

ORD record
ord-6daf8a8dedef405e9b97c0fddcb094f5
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

Loading…