Methanol → Methyl 5-amino-2-thiophenecarboxylate

HRID 726473Notes

Reaction equation

HRID 726473 reaction equation
CO.[N+:3]([C:6]1[S:10][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:7]=1)([O-])=O>[Fe].O>[NH2:3][C:6]1[S:10][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 799082-Thiophenecarboxylic acid, 5-nitro-, methyl ester

Product 1

HCID 7131725Methyl 5-amino-2-thiophenecarboxylateYield 254.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

3.6 g of iron powder, 1.4 g of FeSO4.7H2O, 25 ml of methanol and 8 ml of water were successively introduced into a three-necked flask. 940 mg (5 mmol) of methyl 5-nitro-2-thiophenecarboxylate were then added and the mixture was heated at 70° C. for eight hours. The reaction medium was filtered on celite, the filtrate evaporated, and taken up in water and ethyl ether. The organic phase was decanted, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with dichloromethane; 2 g (77%) of the expected compound of melting point 110°-112° C. were obtained.

Workup

  1. filtrationThe reaction medium was filtered on celite
  2. customthe filtrate evaporated
  3. customThe organic phase was decanted
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customwas purified by chromatography on a silica column
  8. washeluted with dichloromethane

Sources & evidence

ORD record
ord-c0c64d77a2d947b0a4c5e9b6e6cda65e
Source dataset
uspto-grants-1998_01
Patent number
US05709867

Reaction notes

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