2-Pyridinecarboxaldehyde → 500697-36-9

HRID 17787Notes

Reaction equation

HRID 17787 reaction equation
[CH2:1]([C:11]1[CH:17]=[C:16]([CH3:18])[C:14]([NH2:15])=[C:13]([CH3:19])[CH:12]=1)[C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]=O>C(O)C.C(O)=O>[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]=[N:15][C:14]1[C:13]([CH3:19])=[CH:12][C:11]([CH2:1][C:2]2[CH:3]=[C:4]([CH3:10])[C:5]([N:6]=[CH:26][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=3)=[C:7]([CH3:9])[CH:8]=2)=[CH:17][C:16]=1[CH3:18]

Participants

5

Reactant 2

HCID 142732-PyridinecarboxaldehydeHCID 776904,4'-Methylenebis(2,6-xylidine)

Product 1

HCID 68745921500697-36-9Yield 32.9%

Reagents, catalysts & solvents 2

HCID 284Formic AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

To a suspension of 2a (0.50 g, 1.97 mmol) in absolute ethanol (2 ml) was added 2-pyridinecarboxaldehyde (0.56 ml, 5.91 mmol, 3 eq.) and one drop of formic acid. The mixture was stirred at 45° C. overnight. On cooling to room temperature the suspension was filtered, washed with cold ethanol and dried under reduced pressure to afford 17 as a yellow solid (0.28 g, 18%).

Workup

  1. temperatureOn cooling to room temperature the suspension
  2. filtrationwas filtered
  3. washwashed with cold ethanol
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-1dc78b429cd44580a0ac186a679e133f
Source dataset
uspto-grants-2010_06
Patent number
US07741240B2

Reaction notes

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