Methyl 5-chloro-2-(2-phenylpyrrolidin-1-yl)nicotinate → 5-Chloro-2-(2-phenylpyrrolidin-1-yl)nicotinic acid

HRID 72457

Reaktionsgleichung

Reaktionsgleichung von HRID 72457
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8]>CO.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Komponenten

4

Edukt 1

HCID 67958237Methyl 5-chloro-2-(2-phenylpyrrolidin-1-yl)nicotinate

Produkt 1

HCID 679586975-Chloro-2-(2-phenylpyrrolidin-1-yl)nicotinic acidAusbeute 108 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To an ice cooled solution of methyl 5-chloro-2-(2-phenylpyrrolidin-1-yl)nicotinate (D72) (165 mg, 0.520 mmol) in methanol (10 ml), 10N NaOH (10 ml) was added. The mixture was heated under reflux overnight. After cooled to room temperature, the mixture was concentrated in vacuo. The residue was diluted with water (10 ml), acidified with 2.5N HCl (pH 1-2), and the resulting mixture was extracted with ethyl acetate (2×10 ml). The organic solution was washed with brine (20 ml), dried over Na2SO4 and evaporated in vacuo to afford the title compound (D98) (170 mg) as a red solid.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationthe mixture was concentrated in vacuo
  4. additionThe residue was diluted with water (10 ml)
  5. extractionthe resulting mixture was extracted with ethyl acetate (2×10 ml)
  6. washThe organic solution was washed with brine (20 ml)
  7. dry with materialdried over Na2SO4
  8. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-81d088ce54304cf29e2e7ba529ec83ca
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828987B2

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