Picolyl chloride → (Pyridin-2-yl)methyl 2-(2,3-dimethylanilino)benzoate

HRID 979183Notes

Reaction equation

HRID 979183 reaction equation
[C:1]1([NH:9][C:10]2[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12]([O-:14])=[O:13])[CH:6]=[CH:5][CH:4]=[C:3]([CH3:7])[C:2]=1[CH3:8].[Na+].Cl[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1>CN(C)C=O>[N:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH2:21][O:13][C:12](=[O:14])[C:11]1[C:10](=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:9][C:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH3:7])[C:2]=1[CH3:8]

Participants

4

Reactant 2

HCID 23393Picolyl chlorideHCID 23665724Sodium mephenamate

Product 1

HCID 13786689(Pyridin-2-yl)methyl 2-(2,3-dimethylanilino)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 2.36 g amount of sodium N-(2,3-xylyl)anthranilate was dissolved in 20 ml of dimethyl formamide and 1.25 g of 2-chloromethyl pyridine was then added thereto. The mixture was allowed to react at a temperature of 90° C. for 3 hours. After the reaction, the solvent was distilled off in vacuo and the residue was charged with water. The mixture was then extracted with ether. After dehydration, the ether was distilled off and the resultant residue was recrystallized from methanol. Thus, 3.00 g of the desired pale yellow 2-pyridylmethyl-N-(2,3-xylyl)anthranilate having the following physical properties was obtained.

Workup

  1. customto react at a temperature of 90° C. for 3 hours
  2. customAfter the reaction
  3. distillationthe solvent was distilled off in vacuo
  4. additionthe residue was charged with water
  5. extractionThe mixture was then extracted with ether
  6. distillationAfter dehydration, the ether was distilled off
  7. customthe resultant residue was recrystallized from methanol

Sources & evidence

ORD record
ord-9632f8cfe3594fb887a15b6008198194
Source dataset
uspto-grants-1987_05
Patent number
US04666929

Reaction notes

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