2-Pyridinecarboxaldehyde → HCID 178428447, compound

HRID 41331Notes

Reaction equation

HRID 41331 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:3]=1[OH:13].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]=O>CO.C(O)=O>[O:13]([C:3]1[C:4]([C:9]([CH3:10])([CH3:12])[CH3:11])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1/[N:1]=[CH:20]/[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 142732-PyridinecarboxaldehydeHCID 5964582-Amino-6-tert-butyl-4-methyl-phenol

Product 1

HCID 178428447HCID 178428447, compoundYield 107.2%

Reagents, catalysts & solvents 2

HCID 284Formic AcidCatalystHCID 887MethanolSolvent2×

Procedure

To a slurry of 2-amino-4-methyl-6-tertbutylphenol (0.70 g, 3.90 mmol) in 5 mL methanol, a methanol solution of pyridine-2-carbaldehyde (0.418 g, 3.90 mmol) was slowly added, forming a dark orange solution. Two drops formic acid were added, quickly forming a yellow precipitate. This was stirred for 2 hr, then collected on a frit, washed with cold methanol and dried under vacuum to yield 0.72 g of 12 (69%).

Workup

  1. customforming a dark orange solution
  2. customquickly forming a yellow precipitate
  3. customcollected on a frit
  4. washwashed with cold methanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-55891c2509da445aa0e0251560bcca0e
Source dataset
uspto-grants-2013_09
Patent number
US08530593B2

Reaction notes

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