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

HRID 1750784Notes

Reaction equation

HRID 1750784 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-80d82053414b4ed4ad04c2425e0ddde2
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

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