8-Hydroxyquinoline → HCID 69058049, compound

HRID 1819528Notes

Reaction equation

HRID 1819528 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7](Br)=[CH:6][C:3]=1[C:4]#[N:5].[OH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+].OC1C=CC=C2C=1N=CC=C2>CS(C)=O.C(Cl)Cl.[Cu]I>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([N:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]2=[O:11])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

8

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 4297402-Amino-5-bromobenzonitrileHCID 178516071HCID 178516071, compound

Product 1

HCID 69058049HCID 69058049, compoundYield 11.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
160 °C

Procedure

A suspension of 2-amino-5-bromobenzonitrile (1 g), 2-hydroxypyridine (730 mg), CuI (190 mg), potassium carbonate (770 mg) and 8-hydroxyquinoline (150 mg) in 7 ml DMSO was heated for 1.5 h at 160° C. The reaction mixture was afterwards cooled, diluted with CH2Cl2 and filtered through decalite. The organic phase was extracted with water and brine and purified by chromatography (silica gel, AcOEt/heptane) to yield 2-amino-5-(2-oxo-2H-pyridin-1-yl)-benzonitrile as a yellow solid (120 mg). MH+=212.1

Workup

  1. temperatureThe reaction mixture was afterwards cooled
  2. filtrationfiltered through decalite
  3. extractionThe organic phase was extracted with water and brine
  4. custompurified by chromatography (silica gel, AcOEt/heptane)

Sources & evidence

ORD record
ord-89f981ce876d4d7dbcd9337c878cbf42
Source dataset
uspto-grants-2009_10
Patent number
US07601752B2

Reaction notes

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