p-Toluenesulfonic acid → N-2,6-Diisopropylphenylpyridin-2-aldiMin

HRID 532164Notes

Reaction equation

HRID 532164 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[N:6]=[CH:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 142732-PyridinecarboxaldehydeHCID 32484Diisopropylaniline

Product 1

HCID 1284716N-2,6-Diisopropylphenylpyridin-2-aldiMinYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,6-Diisopropylaniline (2.0 g, 11.3 mmol) was added to a solution of picolinaldehyde (1.2 g, 11.3 mmol) in toluene (200 mL) in a round bottom flask equipped with a Dean-Stark trap, followed by the addition of a catalytic amount of p-toluenesulfonic acid (0.1 g). The reaction mixture was refluxed for 18 h to remove water. The reaction mixture was cooled to rt, and then washed once with water (100 mL), and the toluene was removed under reduced pressure. The resulting residue was purified by chromatography on silica gel to give the desired product (1.2 g, 40% yield) as a pale green solid.

Workup

  1. customequipped with a Dean-Stark trap
  2. temperatureThe reaction mixture was refluxed for 18 h
  3. customto remove water
  4. washwashed once with water (100 mL)
  5. customthe toluene was removed under reduced pressure
  6. customThe resulting residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-28a948c9d3aa4361b1f5dd513a568417
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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