Methyl 5-methyl-4-nitrothiophene-2-carboxylate → Methyl 4-amino-5-methylthiophene-2-carboxylate

HRID 2078699Notes

Reaction equation

HRID 2078699 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH3:13])=[C:8]([N+:10]([O-])=O)[CH:9]=1)=[O:4].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH3:13])=[C:8]([NH2:10])[CH:9]=1)=[O:4]

Participants

5

Reactant 2

HCID 268679Methyl 5-methyl-4-nitrothiophene-2-carboxylate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 59640747Methyl 4-amino-5-methylthiophene-2-carboxylateYield 99.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-Methyl-4-nitro-thiophene-2-carboxylic acid methyl ester [15.09 g., 75.0 mM, Intermediate (23)] is dissolved in ethyl acetate (200 mL) to which 10% palladium on charcoal (1.03 g) is added and the mixture is shaken under 50 psi of hydrogen. The catalyst is removed by filtration and the solvent is removed leaving 4-amino-5-methyl-thiophene-2-carboxylic acid methyl ester [12.82 g., 99.8%, Intermediate (24)] as a yellow solid; MS 171.9 (100%, M+1).

Workup

  1. additionis added
  2. customThe catalyst is removed by filtration
  3. customthe solvent is removed

Sources & evidence

ORD record
ord-19cb884d1d1f471bb9b3fc66a9648f88
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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