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

HRID 231641Notes

Reaction equation

HRID 231641 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 77.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Oxo-3-methoxycarbonyltetrahydrothiophene (3.9 g) was heated under reflux for 1 hour with hydroxylamine hydrochloride (2 g) in acetonitrile 10 ml). The mixture was then cooled and the solid portion was filtered off and washed with dry diethyl ether to afford the title compound (3.65 g), m.p. 203°-204° C.

Workup

  1. temperatureThe mixture was then cooled
  2. filtrationthe solid portion was filtered off
  3. washwashed with dry diethyl ether

Sources & evidence

ORD record
ord-ee69670acd5843ca96cce8c411cf44b0
Source dataset
uspto-grants-1989_07
Patent number
US04847386

Reaction notes

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