2-Aminophenol → HCID 1211386, compound

HRID 1457652Notes

Reaction equation

HRID 1457652 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(N(CC)CC)C.Cl.[Cl:17][C:18]1[C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=1>O1CCCC1>[OH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:24]([C:23]1[C:18]([Cl:17])=[N:19][CH:20]=[CH:21][CH:22]=1)=[O:25]

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 8471TriethylamineHCID 234977532-chloro-3-pyridinecarboxylic acid chloride

Product 1

HCID 1211386HCID 1211386, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

As described in J. Med. Chem., 37, 519 (1994), a solution of 1.09 g of 2-aminophenol in 15 ml of tetrahydrofuran is added dropwise to a mixture of 2.1 g of triethylamine and 2.33 g of 2-chloropyridine-3-carbonyl chloride hydrochloride in 10 ml of tetrahydrofuran. The mixture is stirred at room temperature for one hour under argon and then refluxed for one hour. The solvent is removed under vacuum and the residue triturated with water: The solid is filtered off and washed with water to give 1.02 g of solid. Recrystallization from 2-propanol gives crystals, m.p. 145°-146° C.

Workup

  1. temperaturerefluxed for one hour
  2. customThe solvent is removed under vacuum
  3. customthe residue triturated with water
  4. filtrationThe solid is filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-3c5aff55c6c74b3d97a31f910df50f0a
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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