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8-Hydroxyquinoline → HCID 66974111, compound

HRID 499784
Notes
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Reaction equation

HRID 499784 reaction equation
I[C:2]1[CH:10]=[CH:9][C:8]([N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]2=[O:17])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH:18][CH2:19][C:20]1[N:21]=[CH:22][NH:23][CH:24]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[OH:18][CH2:19][C:20]1[N:21]=[CH:22][N:23]([C:2]2[CH:10]=[CH:9][C:8]([N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]3=[O:17])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 66974180HCID 66974180, compoundHCID 178519868HCID 178519868, compound

Product 1

HCID 66974111HCID 66974111, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
130 °C

Procedure

A mixture of 2-iodo-5-(2-oxopyridin-1(2H)-yl)benzoic acid prepared above (220 mg, 0.65 mmol), 4-hydroxymethylimidazole II-1 (126 mg, 1.29 mmol), 8-hydroxyquinoline (19 mg, 0.13 mmol) and K2CO3 (290 mg, 2.10 mmol) in DMSO (2 mL) was degassed with Ar before being charged with CuI (25 mg, 0.13 mmol). The mixture in a sealed tube was heated at 130° C. overnight. It was then purified by HPLC to give 2-(4-(hydroxymethyl)-1H-imidazol-1-yl)-5-(2-oxopyridin-1(2H)-yl)benzoic acid (92 mg). MS 312.1 (M+H).

Workup

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

Sources & evidence

ORD record
ord-6d0ffa88aa0948e9a8833d257f3d8fb5
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