Ammonium Acetate → 4-{2-[4-(beta-D-Galactopyranosyloxy)-3-methoxyphenyl]-vinyl}-1-methylquinolinium iodide

HRID 1588201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1588201
[O:1]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][C:14]=1[O:21][CH3:22])[C@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[I-:23].[CH3:24][N+:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([CH3:35])=[CH:27][CH:26]=1.C([O-])(=O)C.[NH4+].C(Cl)(Cl)Cl.CO>C(O)C>[I-:23].[C@@H:2]1([O:1][C:13]2[CH:18]=[CH:17][C:16]([CH:19]=[CH:35][C:28]3[C:29]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[N+:25]([CH3:24])=[CH:26][CH:27]=3)=[CH:15][C:14]=2[O:21][CH3:22])[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]

Komponenten

6

Edukt 4

HCID 517165Ammonium AcetateHCID 110769741,4-Dimethylquinolinium iodideHCID 115151674-O-(alpha-d-galactopyranosyl)vanillinHCID 21584188Chloroform methanol

Produkt 1

HCID 678266924-{2-[4-(beta-D-Galactopyranosyloxy)-3-methoxyphenyl]-vinyl}-1-methylquinolinium iodide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of 4-formyl-2-methoxyphenyl β-D-galactopyranoside (1c)(0.20 g, 0.63 mmol), 1,4-dimethylquinolinium iodide (0.18 g, 0.63 mmol) and ammonium acetate (0.15 g, 1.9 mmol) in ethanol (20 ml) was heated at 60°-70° C., with stirring for 1 h when t.l.c. (chloroform-methanol, 5:4) indicated that the aldehyde had been completely converted into the almost non-mobile yellow product. The reaction mixture was cooled, and filtered to give a yellow solid which was washed sequentially with ethanol, acetone and ether to give (23c) as mustard yellow solid (0.33 g, 90%), m.p. 216°-220° C. (decomp.), [α]D -17° (c 1, DMOS)(Found: C, 48.89; H, 5.28; N, 2.36. C25H28INO7.2H2O calc.: C, 48.63; H, 5.22; N, 2.27%).

Aufarbeitung

  1. temperaturewas heated at 60°-70° C.
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customto give a yellow solid which
  5. washwas washed sequentially with ethanol, acetone and ether

Quellen und Nachweise

ORD-Eintrag
ord-8084e161dfb04ae8ba3ec971ee7ce07e
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05221606

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