Water → 2-(Chloromethyl)-3-methylpyridine

HRID 2413825Notes

Reaction equation

HRID 2413825 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:9]N1C(=O)N(Cl)C(=O)N(Cl)C1=O.O.[OH-].[K+]>C1CCCCC1.C(N)(=O)C1C=CC=CC=1>[Cl:9][CH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6909Trichloroisocyanuric AcidHCID 114202,3-LutidineHCID 14797Potassium Hydroxide

Product 1

HCID 130586822-(Chloromethyl)-3-methylpyridineYield 107.2%

Reagents, catalysts & solvents 2

HCID 2331BenzamideCatalystHCID 8078CyclohexaneSolvent

Procedure

A mixture of 107.16 g (1 mole) of 2,3-dimethyl-pyridine and 5 g of benzamide in 400 ml of cyclohexane was heated to reflux while adding over 4 hours 130 g (0.56 mole) of trichloroisocyanuric acid (min. 90% available chlorine) in portions and the mixture was stirred for another 7 hours at reflux and then cooled. Under agitation mix with 500 ml of water and 150 ml of 50% potassium hydroxide were added with stirring to obtain a solution. The decanted organic phases were dried over MgSO4 and evaporated to dryness under reduced pressure to obtain 85 g (60%) of 2-chloromethyl-3-methyl pyridine which slowly colored red with a boiling point of 53° to 57° C. at 3 mm H

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureat reflux
  4. temperaturecooled
  5. additionwere added
  6. stirringwith stirring
  7. customto obtain a solution
  8. dry with materialThe decanted organic phases were dried over MgSO4
  9. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-2dd6c9a4644d4e11a5939915d092777e
Source dataset
uspto-grants-1988_01
Patent number
US04719298

Reaction notes

Loading…