Sodium Hydroxide → Thieno[3,2-c]pyridine-6-carboxylic acid

HRID 1072998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072998
[S:1]1[C:9]2[CH:8]=[C:7]([C:10]([O:12]C)=[O:11])[N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.[OH-].[Na+]>CO.O>[S:1]1[C:9]2[CH:8]=[C:7]([C:10]([OH:12])=[O:11])[N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 10954414Thieno[3,2-c]pyridine-6-carboxylic acid, methyl ester

Produkt 1

HCID 12277676Thieno[3,2-c]pyridine-6-carboxylic acidAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Methyl thieno[3,2-c]pyridine-6-carboxylate (C155) (678 mg, 3.5 mmol) is dissolved in MeOH (16 mL) and H2O (2 mL). 2M NaOH (1.8 mL, 3.6 mmol) is added drop-wise, and the solution stirred at rt. After 2 days (complete disappearance of ester by TLC), the solution is concentrated in vacuo. The residue is dissolved in H2O (12 mL), and the pH is adjusted to 3.5 with 10% HCl. The precipitated solid is removed by filtration, and the solid is rinsed with ether, affording thieno[3,2-c]pyridine-6-carboxylic acid (C160) as a white solid (43% yield). HRMS (FAB) calculated for C8H5NO2S+H: 180.0119, found 180.0123 (M+H).

Aufarbeitung

  1. concentrationthe solution is concentrated in vacuo
  2. dissolutionThe residue is dissolved in H2O (12 mL)
  3. customThe precipitated solid is removed by filtration
  4. washthe solid is rinsed with ether

Quellen und Nachweise

ORD-Eintrag
ord-3d7ca39a987b4f4da4979de538c8eb14
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911543B2

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