Picolinic acid → HCID 20446212, compound

HRID 1051566Notes

Reaction equation

HRID 1051566 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([OH:17])=O.[NH2:18][C:19]1[CH:20]=[C:21](O)[CH:22]=[CH:23][C:24]=1[Cl:25].IC1C=CC=CC=1>[Cu]I.CS(C)=O>[Cl:25][C:24]1[CH:23]=[CH:22][C:21]([O:17][C:15]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:20][C:19]=1[NH2:18]

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 50700783-Amino-4-chlorophenol

Product 1

HCID 20446212HCID 20446212, compoundYield 853%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A heat gun-dried 100-mL round bottomed flask equipped with a magnetic stir bar was charged with potassium phosphate (5.91 g, 27.9 mmol), picolinic acid (0.171 g, 1.393 mmol), copper(I) iodide (0.133 g, 0.697 mmol), 3-amino-4-chlorophenol (2.0 g, 13.93 mmol), dimethylsulfoxide (27.9 mL), and iodobenzene (3.41 g, 16.72 mmol). The resulting mixture was heated to 80° C. After 15 h, the reaction mixture was subjected to an aqueous workup to afford the crude product, which was then purified by flash chromatography to afford pure 2-chloro-5-phenoxyaniline (2.61 g, 85%). MS (ESI, pos. ion) m/z 220 [M+1].

Workup

  1. customA heat gun-dried 100-mL round bottomed flask
  2. customequipped with a magnetic stir bar
  3. customto afford the crude product, which
  4. customwas then purified by flash chromatography

Sources & evidence

ORD record
ord-4208f3bceb504e56a49b894ab3e24191
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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