Methyl 3-amino-2-thiophenecarboxylate → Methyl 3-(formylamino)-2-thiophenecarboxylate

HRID 2175378Notes

Reaction equation

HRID 2175378 reaction equation
[C:1]([O-])(=[O:3])C.[NH4+].[NH2:6][C:7]1[CH:11]=[CH:10][S:9][C:8]=1[C:12]([O:14][CH3:15])=[O:13]>C(O)=O>[CH:1]([NH:6][C:7]1[CH:11]=[CH:10][S:9][C:8]=1[C:12]([O:14][CH3:15])=[O:13])=[O:3]

Participants

4

Reactant 2

HCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 517165Ammonium Acetate

Product 1

HCID 2777636Methyl 3-(formylamino)-2-thiophenecarboxylateYield 98.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Formic acid 125 ml, and ammonium acetate (15.9 g, 207 mmol) were added to methyl 3-amino-2-thiophene carboxylate (25 g, 159.04 mmol) and the mixture was refluxed for 4 hours. After lowering the temperature to room temperature, the synthesized solid was washed with water and the title compound (29 g, 98%) was obtained.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customto room temperature
  3. washthe synthesized solid was washed with water

Sources & evidence

ORD record
ord-eba22fafb3644d51a230840e17a1e266
Source dataset
uspto-grants-2015_06
Patent number
US09062066B2

Reaction notes

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