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8-Hydroxyquinoline → HCID 66974180, compound

HRID 499783
Notes
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Reaction equation

HRID 499783 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 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-8582b845691d4dc49bda2ddabf6c6fe4
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07767697B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes