Methanol → 3-Amino-4-methylthiophene-2-carboxylic acid

HRID 1688072

Reaktionsgleichung

Reaktionsgleichung von HRID 1688072
[NH2:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]([O:10]C)=[O:9].[OH-].[Na+].CO>O>[NH2:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]([OH:10])=[O:9]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 123584Methyl 3-amino-4-methylthiophene-2-carboxylate

Produkt 1

HCID 149896783-Amino-4-methylthiophene-2-carboxylic acidAusbeute 84,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-amino-4-methyl-2-thiophene carboxylate (5 g, 29 mmol) and sodium hydroxide (3.5 g, 88 mmol) in a mixed solution (methanol:H2O/30 ml:120 ml) was heated at 50° C. for over night. The solution was cooled to room temperature and extracted with methylene chloride. The aqueous phase was acidified with 6N HCl until pH equal to 5. The aqueous phase was extracted again with ethyl acetate, and solvent phase washed with brine and dried over by sodium sulfate. After filtered and dried over the solvent, evaporated solvent to give 3.85 g of 3-amino-4-methyl-thiophene-2-carboxylic acid as a white solid in 84% yield: 1H NMR (300 MHz, CDCl3) δ 7.05 (d, 1H), 3.12 (br, 2H), 2.16 (s, 3H); MS (m/e): 157.9 (M+1).

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. extractionThe aqueous phase was extracted again with ethyl acetate, and solvent phase
  3. washwashed with brine
  4. dry with materialdried over by sodium sulfate
  5. filtrationAfter filtered
  6. customdried over the solvent
  7. customevaporated solvent

Quellen und Nachweise

ORD-Eintrag
ord-12a02a222cd7427cb0e49e819f666f5f
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148391B2

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