p-Toluenesulfonic acid → HCID 178439035, compound

HRID 1516660Notes

Reaction equation

HRID 1516660 reaction equation
C([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Br:9])[N:4]=1)=O.[CH:10]([C:13]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]([CH3:22])[CH3:21])[C:14]=1[NH2:15])([CH3:12])[CH3:11].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:9][C:5]1[NH:4][C:3](=[N:15][C:14]2[C:16]([CH:20]([CH3:21])[CH3:22])=[CH:17][CH:18]=[CH:19][C:13]=2[CH:10]([CH3:12])[CH3:11])[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 32484DiisopropylanilineHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 178439035HCID 178439035, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A dry, 500 mL 3-neck round bottom flask is charged with a solution of 2-formyl-6-bromopyridine (72.1 g, 383 mmol) and 2,6-diisopropylaniline (72.5 g, 383 mmol) in 500 mL of anhydrous toluene containing 0.3 nm pore size molecular sieves (6 g) and 80 mg of p-TsOH. The reactor is equipped with a condenser, an over head mechanical stirrer and a thermocouple well. The mixture is heated to 70° C. under N2 for 12 h. After filtration and removal of the volatiles under reduced pressure, a brown oil is isolated. Yield was 109 g, 81.9 percent.

Workup

  1. customThe reactor is equipped with a condenser
  2. filtrationAfter filtration and removal of the volatiles under reduced pressure
  3. customa brown oil is isolated

Sources & evidence

ORD record
ord-e3b6bc9cb5774b8187e0c140a5aa7af0
Source dataset
uspto-grants-2012_07
Patent number
US08227546B2

Reaction notes

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