2-Thiophenecarboxylic acid, 5-nitro-, methyl ester → Methyl 5-amino-2-thiophenecarboxylate

HRID 1459439Notes

Reaction equation

HRID 1459439 reaction equation
[N+:1]([C:4]1[S:8][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:5]=1)([O-])=O>CO>[NH2:1][C:4]1[S:8][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 799082-Thiophenecarboxylic acid, 5-nitro-, methyl ester

Product 1

HCID 7131725Methyl 5-amino-2-thiophenecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a Parr flask was added methyl 5-nitrothiophene-2-carboxylate (5.00 g, 26.71 mmol) and MeOH (100 mL). The solution was purged with a stream of Ar, and 5% platinum on sulfide carbon (2.00 g) was added. The mixture was hydrogenated on a Parr apparatus set at 50 psi for 6.5 hours. The reaction was then filtered through celite and the solvents removed in vacuo to yield methyl 5-aminothiophene-2-carboxylate as an olive green oil.

Workup

  1. customThe solution was purged with a stream of Ar, and 5% platinum on sulfide carbon (2.00 g)
  2. additionwas added
  3. filtrationThe reaction was then filtered through celite
  4. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-f7baa62e3f9745608dcf0a29a10ad963
Source dataset
uspto-grants-1998_12
Patent number
US05854245

Reaction notes

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