Diisopropylaniline → HCID 178426832, compound

HRID 499961Notes

Reaction equation

HRID 499961 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]([C:8]2[N:13]=[C:12](C=O)[CH:11]=[CH:10][CH:9]=2)[CH:7]=1.[CH:17]([C:20]1[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]([CH3:29])[CH3:28])[C:21]=1[NH2:22])([CH3:19])[CH3:18]>C(O)=O.CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]([C:8]2[NH:13][C:12](=[N:22][C:21]3[C:23]([CH:27]([CH3:28])[CH3:29])=[CH:24][CH:25]=[CH:26][C:20]=3[CH:17]([CH3:19])[CH3:18])[CH:11]=[CH:10][CH:9]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 32484DiisopropylanilineHCID 136059564HCID 136059564, compound

Product 1

HCID 178426832HCID 178426832, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-(5′-methyl-2′-hydroxyphenyl)-2-formyl-pyridine (4) (640 mg, 3.00 mmol) in the minimum volume of methanol was added 1.5 equivalents of 2,6-diisopropylaniline (780 mg, 4.50 mmol). After the addition of a few drops of formic acid, the solution was stirred overnight. The cloudy yellow reaction mixture was then filtered through a frit, and the solid washed with methanol (3×5 mL), giving 6-(5′-methyl-2′-hydroxyphenyl)-2-(N-(2,6-diisopropylphenyl) imino)pyridine (5) as a yellow solid. Yield: 1.06 g (95%).

Workup

  1. filtrationThe cloudy yellow reaction mixture was then filtered through a frit
  2. washthe solid washed with methanol (3×5 mL)

Sources & evidence

ORD record
ord-78519d320ba2435bb3353fe50893e9d0
Source dataset
uspto-grants-2010_08
Patent number
US07767773B2

Reaction notes

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