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

HRID 1588205
Notes
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Reaction equation

HRID 1588205 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 27504451,2-Dimethylquinolinium iodideHCID 545716624-formyl-2,6-dimethoxyphenyl beta-D-galactopyranoside

Product 1

HCID 678599222-{2-[4-(beta-D-Galactopyranosyloxy)-3,5-dimethoxyphenyl]-vinyl}-1-methylquinolinium iodideYield 86%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

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

  1. customThe dark orange precipitate which formed during the reaction
  2. filtrationwas then filtered off
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes