Water → 31309-58-7

HRID 1906201Notes

Reaction equation

HRID 1906201 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[CH3:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:9][N:10]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7515N-MethylanilineHCID 11430Potassium CarbonateHCID 23393Picolyl chloride

Product 1

HCID 1421163431309-58-7Yield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-chloromethylpyridine (50 g), N-methylaniline (42 g), and potassium carbonate (120 g) in N,N-dimethylformamide (200 ml) was stirred for 4 hours at 120° C. The reaction mixture was cooled to room temperature, added to water (1 l), and extracted with ether. The ether extract was washed with water and then treated with activated carbon. After drying over magnesium sulfate, the ether extract was filtered and concentrated. The residue was crystallized from isopropyl alcohol to give N-methyl-N-(2-pyridylmethyl)aniline (39 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. additiontreated with activated carbon
  6. dry with materialAfter drying over magnesium sulfate
  7. extractionthe ether extract
  8. filtrationwas filtered
  9. concentrationconcentrated
  10. customThe residue was crystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-bbfa271d7f044856993083f5cf71c13e
Source dataset
uspto-grants-1987_03
Patent number
US04650804

Reaction notes

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