Sodium Hydroxide → 5-Chloro-2-(3-phenoxyazetidin-1-yl)nicotinic acid

HRID 72459

Reaktionsgleichung

Reaktionsgleichung von HRID 72459
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:15][CH:14]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+]>CO.O1CCCC1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:15][CH:14]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 67958085Methyl 5-chloro-2-(3-phenoxyazetidin-1-yl)nicotinate

Produkt 1

HCID 679582405-Chloro-2-(3-phenoxyazetidin-1-yl)nicotinic acidAusbeute 95,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

Methyl 5-chloro-2-(3-phenoxyazetidin-1-yl)nicotinate (D75) (305 mg, 0.96 mmol) was dissolved in methanol/tetrahydrofuran (10 ml/10 ml), 5N NaOH (10 ml) was added at 0° C. The resulting reaction mixture was heated to 35° C. for 18 hours then cooled to room temperature and concentrated. Water added (10 ml) and the mixture was acidified with 2.5N HCl (pH1-2). The white solid was collected, washed with water and dried to provide compound (D101) (280 mg) as a white solid.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturethen cooled to room temperature
  3. concentrationconcentrated
  4. additionWater added (10 ml)
  5. customThe white solid was collected
  6. washwashed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-fe99e9abad004c64a116bd86fea4ef4b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828987B2

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