8-Hydroxyquinoline → HCID 66974180, compound

HRID 1802597Notes

Reaction equation

HRID 1802597 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][C:9](I)=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.OC1C=CC=C2C=1N=CC=C2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[I:1][C:2]1[CH:11]=[CH:10][C:9]([N:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]2=[O:13])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 62657Potassium Phosphate, TribasicHCID 10883593Benzoic acid, 2,5-diiodo-, methyl esterHCID 178516071HCID 178516071, compound

Product 1

HCID 66974180HCID 66974180, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of methyl 2,5-diiodobenzoate prepared above (1.04 g, 2.67 mmol), 2-hydroxypyridine 1-7 (0.254 g, 2.67 mmol), 8-hydroxyquinoline (0.077 g, 0.53 mmol) and K3PO4 (1.13 g, 5.33 mmol) in dioxane (8 mL) was degassed with Ar before being charged with CuI (0.101 g, 0.53 mmol). The mixture in a sealed tube was heated at 130° C. overnight. It was then purified by HPLC to give 2-iodo-5-(2-oxopyridin-1(2H)-yl)benzoic acid (0.220 g). MS 342.0 (M+H).

Workup

  1. customwas degassed with Ar
  2. customIt was then purified by HPLC

Sources & evidence

ORD record
ord-ff0cc42209d04213b964435a0e350c01
Source dataset
uspto-grants-2013_01
Patent number
US08349873B2

Reaction notes

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