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

HRID 2297750Notes

Reaction equation

HRID 2297750 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 86.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
22.5 °C

Procedure

To a solution of 3-amino-thiophene-2-carboxylic acid methyl ester (25 g, 159 mmol) in 125 mL of formic acid was added ammonium acetate (15.9 g, 207 mmol). The reaction mixture was heated to reflux for 3 hours after which time the solution was cooled to room temperature (20-25° C.). The solid that formed was filtered, washed with water, and dried in vacuo to afford 25.4 g (86%) of 3-formylamino-thiophene-2-carboxylic acid methyl ester. 1H NMR (400 MHz, DMSO) d 10.2 (s, 1H), 8.35 (s, 3H), 7.92 (d, 1H), 7.91 (d, 1H), 3.76 (s, 3H). LC-MS: 186 (MH+); HPLC RT: 2.81 minutes.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours after which time the solution
  3. customThe solid that formed
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-45f9b0b517504b3c848a0fabc7a20338
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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