2-Aminophenol → N-(2-hydroxyphenyl)-4,5,6-trichloropyridine-2-carboxamide

HRID 1837449Notes

Reaction equation

HRID 1837449 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10](Cl)=[O:11])[CH:3]=1.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20].C(N(CC)CC)C>ClCCl>[OH:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[NH:13][C:10]([C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=1)=[O:11]

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 8471TriethylamineHCID 129936934,5,6-Trichloropicolinoyl chloride

Product 1

HCID 22677386N-(2-hydroxyphenyl)-4,5,6-trichloropyridine-2-carboxamideYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4,5,6-trichloropyridine-2-carbonyl chloride (1.0 g, 4.1 mmol) in dichloromethane (10 mL) was added dropwise to a solution of 2-aminophenol (0.45 g, 4.1 mmol) and triethylamine (0.6 mL) in dichloromethane (30 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for an additional thirty minutes. The solvents were removed and the residue partitioned between 20% tetrahydrofuran/ethyl acetate and 1M hydrochloric acid. The organic layer was separated, washed with saturated sodium bicarbonate, brine, dried (MgSO4) and concentrated to provide N-(2-hydroxyphenyl)-4,5,6-trichloropyridine-2-carboxamide (1.26 g, 4.0 mmol), mp 240° C. (dec).

Workup

  1. customThe solvents were removed
  2. customthe residue partitioned between 20% tetrahydrofuran/ethyl acetate and 1M hydrochloric acid
  3. customThe organic layer was separated
  4. washwashed with saturated sodium bicarbonate, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f07533cdc84b4ceca296e3b2f3d1421c
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

Loading…