Water → 2-(6-Chloropyridin-3-ylamino)-5-methylbenzoic acid

HRID 42002

Reaktionsgleichung

Reaktionsgleichung von HRID 42002
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Br[C:10]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].C([O-])([O-])=O.[K+].[K+].O>COCCOC>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:10]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:11]=2[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 793055-Amino-2-chloropyridineHCID 2280802-Bromo-5-methylbenzoic acid

Produkt 1

HCID 866572542-(6-Chloropyridin-3-ylamino)-5-methylbenzoic acidAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 6-chloropyridin-3-amine (11.67 mmol, 1.5 g) and 2-bromo-5-methylbenzoic acid (23.34 mmol, 5.02 g), Cu (1.17 mmol, 0.1 g), Cu2O (0.58 mmol, 0.1 g) and K2CO3 (23.34 mmol, 3.2 g) in 1,2-dimethoxyethane (15 ml) was heated at 130° C. for 16 hours, under argon atmosphere. Water was added and the mixture was filtered through celite. HCl 2N aqueous solution was added until pH 6 and the solid formed was filtered off. The crude was purified by chromatography eluting with DCM/MeOH mixtures affording 1.40 g (yield 46%).

Aufarbeitung

  1. filtrationthe mixture was filtered through celite
  2. additionHCl 2N aqueous solution was added until pH 6
  3. customthe solid formed
  4. filtrationwas filtered off
  5. customThe crude was purified by chromatography
  6. washeluting with DCM/MeOH
  7. custommixtures affording 1.40 g (yield 46%)

Quellen und Nachweise

ORD-Eintrag
ord-ed1c3d76e4334931a3392edaa263a26b
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536165B2

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