4-Methoxybenzylamine → 2-((4-Methoxybenzyl)amino)isonicotinonitrile

HRID 887633Notes

Reaction equation

HRID 887633 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6].[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH2:17])=[CH:14][CH:13]=1.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH:17][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=2)[C:5]#[N:6])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 754524-MethoxybenzylamineHCID 516892Sodium BicarbonateHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 219613782-((4-Methoxybenzyl)amino)isonicotinonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To pyridine (500 mL) were added 2-chloroisonicotinonitrile (22.0 g, 159 mmole), para-methoxybenzylamine (25 g, 114% Meq.), and NaHCO3 (30 g). The mixture was heated under reflux overnight. After cooling to RT, the mixture was filtered and the filter cake was rinsed with CH2Cl2. The combined filtrate was concentrated to dryness in vacuum to form a yellow solid. This solid is then recrystallized in EtOAc to give a light yellow crystalline compound and the mother liquor was concentrated and subjected to EtOAc again (repeating three times) to yield the desired compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. filtrationthe mixture was filtered
  4. washthe filter cake was rinsed with CH2Cl2
  5. concentrationThe combined filtrate was concentrated to dryness in vacuum
  6. customto form a yellow solid
  7. customThis solid is then recrystallized in EtOAc
  8. customto give a light yellow crystalline compound
  9. concentrationthe mother liquor was concentrated

Sources & evidence

ORD record
ord-c0107d9b7db142a29d6e52ac62614157
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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