Methyl Methanesulfonate → 5-(3-Bromophenyl)-4-methoxy-1-methyl-3-phenylpyridinium methanesulfonate

HRID 46584

Reaction equation

HRID 46584 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:21])[C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][N:12]([CH3:14])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:22][S:23]([O:26]C)(=[O:25])=[O:24].N1C=CC=C[C:29]1=O>C1C=CC=CC=1>[CH3:22][S:23]([O-:26])(=[O:25])=[O:24].[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([O:21][CH3:29])=[C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:11]=[N+:12]([CH3:14])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 4156Methyl MethanesulfonateHCID 88712-PyridoneHCID 128792753-(3-Bromophenyl)-1-methyl-5-phenylpyridin-4(1H)-one

Product 1

HCID 233457405-(3-Bromophenyl)-4-methoxy-1-methyl-3-phenylpyridinium methanesulfonate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4.0 g. of 5-(3-bromophenyl)-1-methyl-3-phenyl-4(1H)-pyridinone and 20 ml. of methyl methanesulfonate in benzene was heated under reflux for 6 hours. The mixture was cooled and the solvent removed in vacuo. The product failed to crystallize. The product was passed over a silica gel column in ethyl acetate. After the front-running spot was removed the column was flushed with ethanol. The ethanol fractions were again placed on a silica gel solumn and front-running impurities removed. The column was flushed with ethanol and the ethanol removed to yield 0.75 g. of a hard glass. The nmr spectrum of the product was consistent with the structure of the expected salt. For example, there was an N-CH3 peak at 4.4 ppm and a peak at 8.7 ppm attributed to the hydrogens at the 2- and 6-positions of the pyridine ring. As is characteristic of pyridinium salts, both these peaks were shifted from the corresponding peaks in the starting pyridinone.

Workup

  1. additionA mixture of 4.0 g
  2. temperatureunder reflux for 6 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent removed in vacuo
  5. customto crystallize
  6. customAfter the front-running spot was removed the column
  7. customwas flushed with ethanol
  8. customremoved
  9. customThe column was flushed with ethanol
  10. customthe ethanol removed
  11. customto yield 0.75 g

Sources & evidence

ORD record
ord-9e709ebce1a544d6b4a822e4169660cd
Source dataset
uspto-grants-1979_11
Patent number
US04174209

Linked notes

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