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

HRID 1192293Notes

Reaction equation

HRID 1192293 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH2:10])=[O:4].[C:11]([O-])(=[O:13])C.[NH4+]>C(O)=O>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][CH:11]=[O:13])=[O:4]

Participants

4

Reactant 2

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

Product 1

HCID 2777636Methyl 3-(formylamino)-2-thiophenecarboxylateYield 87.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a solution of 3-aminothiophene-2-carboxylic methyl ester (20 g, 127 mmol) in formic acid (100 mL) was added ammonium acetate (13 g, 169 mmol). The mixture was refluxed for 3 hours. After cooling to room temperature, the precipitate was filtered, washed with water and dried under vacuum to afford 3-formylaminothiophene-2-carboxylic acid methyl ester (20.5 g, 87%). 1H NMR (DMSO, 400 Hz) δ 10.38 (s, 1H), 8.42 (s, 1H), 8.00 (d, J=5.2 Hz, 1H), 7.90 (d, J=5.6 Hz, 1H), 3.84 (s, 3H). MS (ESI+) [M+H]+ 186.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. filtrationthe precipitate was filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-91c3ba23cf774011a1127e09f59fb4b0
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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