Ammonium Acetate → 2-{2-[4-(beta-D-Galactopyranosyloxy)-3,5-dimethoxyphenyl]-vinyl}-1-methylquinolinium iodide

HRID 1588205Notes

Reaction equation

[O:1]([C:13]1[C:18]([O:19][CH3:20])=[CH:17][C:16]([CH:21]=O)=[CH:15][C:14]=1[O:23][CH3:24])[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-:25].[CH3:26][N+:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][C:28]=1[CH3:37].C([O-])(=O)C.[NH4+]>C(O)C>[I-:25].[C@@H:2]1([O:1][C:13]2[C:18]([O:19][CH3:20])=[CH:17][C:16]([CH:21]=[CH:37][C:28]3[CH:29]=[CH:30][C:31]4[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=4)[N+:27]=3[CH3:26])=[CH:15][C:14]=2[O:23][CH3:24])[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]

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 4-formyl-2,6-dimethoxyphenyl β-D-galactopyranoside (0.19 g, 0.55 mmol), 1,2-dimethylquinolinium iodide (0.16 g, 0.55 mmol) in ethanol (20 ml) containing ammonium acetate (0.13 g, 1.7 mmol) was stirred at about 60° C. for 5 h. The dark orange precipitate which formed during the reaction was then filtered off and washed with ethanol followed by acetone to give (22c)(0.2 g, 86%) as an orange powder.

Workup

customThe dark orange precipitate which formed during the reaction
filtrationwas then filtered off
washwashed with ethanol

Sources & evidence

ORD record: ord-61c0f1ca792847b79bb086991c74e63a
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05221606

Reaction notes

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