Ammonia → Methyl 4-aminothiophene-3-carboxylate

HRID 2380803Notes

Reaction equation

HRID 2380803 reaction equation
Cl.[NH2:2][C:3]1[C:4]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][S:6][CH:7]=1.N>O>[NH2:2][C:3]1[C:4]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][S:6][CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 2777609Methyl 4-aminothiophene-3-carboxylate Hydrochloride

Product 1

HCID 2777610Methyl 4-aminothiophene-3-carboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 4-aminothiophene-3-carboxylate hydrochloride (290 mg) was dissolved in water (20 mL) and basified with ammonia solution. The solution was extracted with chloroform and the combined chloroform layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent to give the product as pale yellow color oil (150 mg, 65%). 1H NMR (400 MHz, CDCl3): δ 7.92 (1H, d, J=3.6 Hz), 6.08 (1H, d, J=3.6 Hz), 4.79 (2H, br s), 3.85 (3H, s).

Workup

  1. extractionThe solution was extracted with chloroform
  2. washthe combined chloroform layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe solution was filtered
  5. customevaporated the solvent

Sources & evidence

ORD record
ord-9d75b84e991d4bfeb9143586b11b1cb4
Source dataset
uspto-grants-2012_09
Patent number
US08258119B2

Reaction notes

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