3-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl ester → Methyl 4-aminothiophene-3-carboxylate Hydrochloride

HRID 2380802Notes

Reaction equation

HRID 2380802 reaction equation
O=[C:2]1[CH2:6][S:5][CH2:4][CH:3]1[C:7]([O:9][CH3:10])=[O:8].[ClH:11].[NH2:12]O>C(#N)C>[ClH:11].[NH2:12][C:2]1[C:3]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][S:5][CH:6]=1

Participants

4

Reactant 2

HCID 984243-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl esterHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 2777609Methyl 4-aminothiophene-3-carboxylate HydrochlorideYield 62.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-oxo-3-methoxycarbonyltetrahydrothiophene (6.5 g, 40.62 mmol), hydroxylamine hydrochloride (2.84 g, 40.62 mmol) and acetonitrile (30 mL) was stirred under reflux for 1 h. The mixture was then cooled and the solid which separated was filtered off and washed with dry ether to afford the title compound (4.9 g, 62%), mp 192-196° C.

Workup

  1. temperatureunder reflux for 1 h
  2. temperatureThe mixture was then cooled
  3. customthe solid which separated
  4. filtrationwas filtered off
  5. washwashed with dry ether

Sources & evidence

ORD record
ord-bb1974f398bd452badbf5f9c40c8cd3f
Source dataset
uspto-grants-2012_09
Patent number
US08258119B2

Reaction notes

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