2-Amino-3-Hydroxypyridine → 2-Amino-3-(2-methoxybenzyloxy)pyridine

HRID 2231194Notes

Reaction equation

HRID 2231194 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13]Cl>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].[OH-].[Na+].C(Cl)Cl>[NH2:1][C:2]1[C:7]([O:8][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[O:10][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 281142-Amino-3-HydroxypyridineHCID 814952-(Chloromethyl)anisole

Product 1

HCID 102632412-Amino-3-(2-methoxybenzyloxy)pyridineYield 38.1%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a mixture of 2-amino-3-hydroxypyridine (7.64 g) and Adogen 464 (Trademark: prepared by Aldrich Chemical Co.) (0.42 g) in 40% aqueous sodium hydroxide (35 ml) and methylene chloride (35 ml) was added 2-methoxybenzyl chloride (10.87 g) at ambient temperature. After being stirred for 22 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-methoxybenzyloxy)pyridine (6.09 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-2022aea29c484e80a7c9f683cac80b42
Source dataset
uspto-grants-1988_11
Patent number
US04782055

Reaction notes

Loading…