p-Toluenesulfonic acid → HCID 13079834, compound

HRID 2418645Notes

Reaction equation

HRID 2418645 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11]([CH3:14])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[C:18]1(C)[CH:23]=CC(S(O)(=O)=O)=C[CH:19]=1>C(O)CC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:15]([O:17][CH2:19][CH2:18][CH3:23])=[O:16])[C:11]([CH3:14])=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 13079828HCID 13079828, compound

Product 1

HCID 13079834HCID 13079834, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

5-(p-Chlorophenyl)-2-methyl-3-pyridine carboxylic acid (2 gm) and p-toluenesulphonic acid (1.69 g) in n-propanol (125 ml) was refluxed for 15 hours. The solution was concentrated and the residue partitioned between methylene dichloride and aqueous sodium carbonate. The organic phase was separated, washed with water, dried and concentrated to an oil which slowly crystallised to give the title compound (0.66 g), m.p. 54°-7°.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue partitioned between methylene dichloride and aqueous sodium carbonate
  3. customThe organic phase was separated
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated to an oil which
  7. customslowly crystallised

Sources & evidence

ORD record
ord-e1ff9fe521ab48818aceda1fb59471fe
Source dataset
uspto-grants-1984_09
Patent number
US04473395

Reaction notes

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