Ethyl Nicotinate → 1-Benzoyloxymethyl-3-carboethoxypyridinium chloride

HRID 4717

Reaktionsgleichung

Reaktionsgleichung von HRID 4717
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:12]([O:20][CH2:21][Cl:22])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[Cl-:22].[C:12]([O:20][CH2:21][N+:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:1]([O:9][CH2:10][CH3:11])=[O:8])[CH:3]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

3

Edukt 2

HCID 69188Ethyl NicotinateHCID 79257Chloromethyl benzoate

Produkt 1

HCID 141281951-Benzoyloxymethyl-3-carboethoxypyridinium chloride

Versuchsvorschrift

A mixture of 3.00 g (0.02 mol) ethyl nicotinate and 3.50 g (0.02 mol) chloromethyl benzoate was heated at 70° under nitrogen for 10 hrs. Trituration in anhydrous ether and recrystallization from ethanol-ether gave 2.18 g (0.007 mol), 35%, 1-benzoyloxymethyl-3-carboethoxypyridinium chloride, mp 138°-141°; ir (KBr) 1730 cm-1 ; pmr (CDCl3) δ 1.43 (t, 3H), 4.47 (q, 2H), 7.7-7.3 (m, 5H), 8.2-7.95 (m, 2H), 9.17-8.50 (m, 4), 10.0 (bs, 1H) and 10.2 (bd, 1H) ppm.

Aufarbeitung

  1. temperaturewas heated at 70° under nitrogen for 10 hrs
  2. customTrituration in anhydrous ether and recrystallization from ethanol-ether

Quellen und Nachweise

ORD-Eintrag
ord-b567ad629031415c975ad17d8c230aff
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727151

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