alpha-Chloro-o-xylene → 3-[(2-Methylphenyl)methoxy]pyridin-2-amine

HRID 4291

Reaction equation

HRID 4291 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH2:12]Cl>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].[OH-].[Na+].C(Cl)Cl>[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH3:12])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 11093alpha-Chloro-o-xyleneHCID 281142-Amino-3-Hydroxypyridine

Product 1

HCID 138258823-[(2-Methylphenyl)methoxy]pyridin-2-amine

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a mixture of 2-amino-3-hydroxypyridine (7 g) and Adogen 464 (Trademark: prepared by Aldrich Chemical Co.) (0.4 g) in 40% aqueous sodium hydroxide (32 ml) and methylene chloride (32 ml) was added 2-methylbenzyl chloride (8.42 ml) at ambient temperature. After being stirred for 24 hours, the organic layer was separated and the aqueous layer was extracted with methylene chloride. The combined extracts were washed with saturated sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated in vacuo. The crystalline residue was recrystallized from ethyl acetate to give 2-amino-3-(2-methylbenzyloxy)pyridine (7.56 g).

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with methylene chloride
  3. washThe combined extracts were washed with saturated sodium chloride aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe crystalline residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4a0ab28d099d4c989edf76e5c61389c1
Source dataset
uspto-grants-1988_02
Patent number
US04725601

Linked notes

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