HCID 821687, compound → HCID 18350683, compound

HRID 1737264Notes

Reaction equation

HRID 1737264 reaction equation
[C:1]([NH:4][C:5]1[C:9]([C:10]([O:12]C)=[O:11])=[CH:8][S:7][CH:6]=1)(=[O:3])[CH3:2]>[OH-].[K+]>[C:1]([NH:4][C:5]1[C:9]([C:10]([OH:12])=[O:11])=[CH:8][S:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 821687HCID 821687, compound

Product 1

HCID 18350683HCID 18350683, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Methyl 3-acetamidothiophene-4-carboxylate (10.0 g, 50.25 mmol) was added to a 5% methanolic potassium hydroxide solution (100 mL). The mixture was refluxed 2 hours, cooled, and concentrated. The residue was dissolved in water and the acidity was adjusted to pH 1 by addition of 1 N hydrochloric acid (HCl). The precipitate was collected, washed with water, and air dried to afford 8.66 g (93%) of 3-acetamidothiophene-4-carboxylic acid.

Workup

  1. temperatureThe mixture was refluxed 2 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in water
  5. additionthe acidity was adjusted to pH 1 by addition of 1 N hydrochloric acid (HCl)
  6. customThe precipitate was collected
  7. washwashed with water, and air
  8. customdried

Sources & evidence

ORD record
ord-d3423b975f8c4f9fa6020c4d16b8289d
Source dataset
uspto-grants-1999_10
Patent number
US05962457

Reaction notes

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