Isonicotinic Acid → 2-Saccharinylmethyl pyridine-4-carboxylate

HRID 864755

Reaktionsgleichung

Reaktionsgleichung von HRID 864755
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Br[CH2:11][N:12]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[S:13]1(=[O:15])=[O:14].C(N(CC)CC)C>C1(C)C(C)=CC=CC=1>[N:5]1[CH:6]=[CH:7][C:2]([C:1]([O:9][CH2:11][N:12]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[S:13]2(=[O:14])=[O:15])=[O:8])=[CH:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 5922Isonicotinic AcidHCID 8471TriethylamineHCID 15225519N-Bromomethylsaccharin

Produkt 1

HCID 98617952-Saccharinylmethyl pyridine-4-carboxylateAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture of isonicotinic acid (0.98 g, 0.008 mol), 2-bromomethylsaccharin (2.11 g, 0.008 mol), triethylamine (0.81 g, 0.008 mol) and xylene (25 ml) were refluxed for 1 hour. The solvent was removed in vacuo and the residue was partitioned between water and methylene chloride. The organic layer was separated and the solvent removed in vacuo. The solid residue was recrystallized from CH3CN to afford 0.9 g (37%) of 2-saccharinylmethyl pyridine-4-carboxylate as a yellow solid, m.p. 145°-146° C.

Aufarbeitung

  1. temperaturewere refluxed for 1 hour
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between water and methylene chloride
  4. customThe organic layer was separated
  5. customthe solvent removed in vacuo
  6. customThe solid residue was recrystallized from CH3CN

Quellen und Nachweise

ORD-Eintrag
ord-6457aa1183e04a4099e7ab2d812163ed
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05563163

Verknüpfte Notizen

Wird geladen…