Ammonia → 4-{2-[4-(2-acetamido-2-deoxy-beta-D-glucopyranosyloxy)-3-methoxyphenyl]-vinyl}-1-methylquinolinium iodide

HRID 1588202Notes

Reaction equation

HRID 1588202 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:21]([OH:22])[C@H:20]([OH:23])[C@@H:19]([CH2:24][OH:25])[O:18][C@H:6]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][C:9]=1[O:16][CH3:17])(=[O:3])[CH3:2].[I-:26].[CH3:27][N+:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([CH3:38])=[CH:30][CH:29]=1.C([O-])(=O)C.[NH4+].N>C(O)C.C(Cl)(Cl)Cl.CO>[I-:26].[C:1]([NH:4][C@@H:5]1[C@@H:21]([OH:22])[C@H:20]([OH:23])[C@@H:19]([CH2:24][OH:25])[O:18][C@H:6]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[CH:38][C:31]2[C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[N+:28]([CH3:27])=[CH:29][CH:30]=2)=[CH:10][C:9]=1[O:16][CH3:17])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 517165Ammonium AcetateHCID 52931324-Formyl-2-methoxyphenyl 2-acetamido-2-deoxy-beta-glucopyranosideHCID 110769741,4-Dimethylquinolinium iodide

Product 1

HCID 678599714-{2-[4-(2-acetamido-2-deoxy-beta-D-glucopyranosyloxy)-3-methoxyphenyl]-vinyl}-1-methylquinolinium iodide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21584188Chloroform methanolSolvent

Procedure

A stirred suspension of 4-formyl-2-methoxyphenyl 2-acetamido-2deoxy-β-D-glucopyranoside (1b)(0.25 g, 0.70 mmol), 1,4-dimethylquinolinium iodide (0.20 g, 0.70 mmol) in ethanol (20 ml) containing ammonium acetate (0.16 g, 2.1 mmol) and ammonia (conc.) (0.12 ml) was heated at 60°-70° C. The mixture soon turned orange and reaction was complete after 1.5 h as indicated by t.l.c. (chloroform-methanol, 5:4). The solid material was filtered off and washed sequentially with ethanol, acetone and ether to give (23b) as a fine yellow solid {0.34 g, 78%, m.p. 207°-212° C. (decomp.), [α]D +28° (c 1, DMOS)}(Found: C, 52.12; H, 5.01; N, 4.78. C27H31IN2O7 calc. C, 52.10; H, 5.02; N, 4.50%).

Workup

  1. temperaturewas heated at 60°-70° C
  2. customThe mixture soon turned orange and reaction
  3. filtrationThe solid material was filtered off
  4. washwashed sequentially with ethanol, acetone and ether

Sources & evidence

ORD record
ord-a12d292124174d40b1d5ebe196e0bf99
Source dataset
uspto-grants-1993_06
Patent number
US05221606

Reaction notes

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