Water → 2-(6-Bromopyridin-3-ylamino)-5-chlorobenzoic acid

HRID 42043

Reaktionsgleichung

Reaktionsgleichung von HRID 42043
[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Cl[C:10]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].C([O-])([O-])=O.[K+].[K+].O>COCCOC>[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:10]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:11]=2[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 57842,5-Dichlorobenzoic acidHCID 11430Potassium CarbonateHCID 6428116-Bromopyridin-3-amine

Produkt 1

HCID 866572592-(6-Bromopyridin-3-ylamino)-5-chlorobenzoic acidAusbeute 34,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 6-bromopyridin-3-amine (27.27 mmol, 4.70 g), 2,5-dichlorobenzoic acid (54.34 mmol, 10.38 g), Cu (2.71 mmol, 0.2 g), Cu2O (1.36 mmol, 0.2 g) and K2CO3 (54.27 mmol, 7.5 g) in 1,2-dimethoxiethane (40 ml) was heated in a microwave oven at 130° C. for 14 hours, under nitrogen atmosphere. Water was added and the mixture was filtered through celite and extracted with AcOEt. The organic phase was washed with saturated K2CO3 aqueous solution and brine. The solvent was evaporated to afford 3.08 g (yield 31%) of the expected product.

Aufarbeitung

  1. filtrationthe mixture was filtered through celite
  2. extractionextracted with AcOEt
  3. washThe organic phase was washed with saturated K2CO3 aqueous solution and brine
  4. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-5fc2bee7eea0409d8f13fead24c1c4c6
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536165B2

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