Sodium Hydroxide → 3-(2,5-Dimethyl-pyrrol-1-yl)-5,6-bis-trifluoromethyl-pyridine-2-carboxylic acid

HRID 887877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 887877
C[O:2][C:3]([C:5]1[C:10]([N:11]2[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]2[CH3:17])=[CH:9][C:8]([C:18]([F:21])([F:20])[F:19])=[C:7]([C:22]([F:25])([F:24])[F:23])[N:6]=1)=[O:4].[OH-].[Na+]>CO>[CH3:16][C:15]1[N:11]([C:10]2[C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]([C:22]([F:25])([F:23])[F:24])=[C:8]([C:18]([F:19])([F:20])[F:21])[CH:9]=2)[C:12]([CH3:17])=[CH:13][CH:14]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 866576693-(2,5-Dimethyl-pyrrol-1-yl)-5,6-bis-trifluoromethyl-pyridine-2-carboxylic acid methyl ester

Produkt 1

HCID 584423653-(2,5-Dimethyl-pyrrol-1-yl)-5,6-bis-trifluoromethyl-pyridine-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution 3-(2,5-dimethyl-pyrrol-1-yl)-5,6-bis-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (1.28 g, 3.49 mmol) in methanol (25 ml) was added 1M NaOH (7 ml, 6.99 mmol) and the reaction mixture was left to stir at RT for 30 min. The solvent was removed in vacuo and water (20 ml) was added to the remaining residue. The pH was adjusted to pH 4/5 by the addition of 1M HCl. The mixture was extracted with EtOAc (3×20 ml) and the combined organic extracts were washed with brine (30 ml), dried (MgSO4) and concentrated in vacuo and dried in a vacuum oven (50° C.) overnight to give the crude title product as an orange solid which was used without further purification; LC-MS: Rt 1.23 min; MS m/z 353.1 [M+H]+; Method 2minLC_v003.

Aufarbeitung

  1. waitthe reaction mixture was left
  2. customThe solvent was removed in vacuo and water (20 ml)
  3. additionwas added to the remaining residue
  4. additionThe pH was adjusted to pH 4/5 by the addition of 1M HCl
  5. extractionThe mixture was extracted with EtOAc (3×20 ml)
  6. washthe combined organic extracts were washed with brine (30 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customdried in a vacuum oven (50° C.) overnight

Quellen und Nachweise

ORD-Eintrag
ord-e962b3420eaf42dfb083d9eac1fa66f4
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247436B2

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