Ammonium Acetate → 4-[2(4-Benzoyloxy-3,5-dimethoxyphenyl)-vinyl]-1-methylquinolinium iodide

HRID 1588199Notes

Reaction equation

HRID 1588199 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:10](=O)[C:11]1[CH:21]=[C:18]([O:19][CH3:20])[C:16](O)=[C:13]([O:14][CH3:15])[CH:12]=1.[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(O)C>[I-:23].[C:1]([O:9][C:16]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([CH:10]=[CH:35][C:28]2[C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[N+:25]([CH3:24])=[CH:26][CH:27]=2)=[CH:21][C:18]=1[O:19][CH3:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 110769741,4-Dimethylquinolinium iodideHCID 86746982Syringaldehyde benzoate

Product 1

HCID 678267874-[2(4-Benzoyloxy-3,5-dimethoxyphenyl)-vinyl]-1-methylquinolinium iodideYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of syringaldehyde benzoate (2e)(0.18 g, 0.63 mmol), 1,4-dimethylquinolinium iodide (0.18 g, 0.63 mmol) and ammonium acetate (0.15 g, 1.9 mmol) was dissolved in warm ethanol and heated under reflux. The solution rapidly turned yellow and within 15 min, yellow precipitate formed. The reaction was continued for a further 1 h and then filtered. The collected solid was washed with methanol to give (24e)(0.28 g, 81%) as a fine yellow powder, m.p. decomp.>250° C. (Found: C, 58.86; H, 4.25; N, 2.71. C27H24NO4I calc. C., 58.60; H, 4.37; N, 2.53%).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customyellow precipitate formed
  4. waitThe reaction was continued for a further 1 h
  5. filtrationfiltered
  6. washThe collected solid was washed with methanol

Sources & evidence

ORD record
ord-8602509ab8df4822af7238b0d3b8e043
Source dataset
uspto-grants-1993_06
Patent number
US05221606

Reaction notes

Loading…