Biphenyl → 2-Hydroxyquinoline

HRID 479581Notes

Reaction equation

HRID 479581 reaction equation
[NH:1](/[CH:8]=[C:9](/[C:15]1C=CC=CC=1)\C(OCC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C2C=CC=CC=2)C=CC=CC=1.C1([O:39]C2C=CC=CC=2)C=CC=CC=1>>[NH:1]1[C:2]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:15]=[CH:9][C:8]1=[O:39]

Participants

4

Reactant 3

HCID 7095BiphenylHCID 7583Diphenyl EtherHCID 10754305HCID 10754305, compound

Product 1

HCID 60382-HydroxyquinolineYield 144%

Conditions

Temperature
250 °C

Procedure

Compound 1 (1.10 g, 4.11 mmol) is added portionwise and rapidly with stirring, to a solution of biphenyl (1.70 g) and diphenyl ether (13.10 g) heated to 250° C. After 10 minutes, the heating is stopped. During the cooling, the quinolone 2 precipitates out in the reaction medium. This product is collected by filtration and then rinsed with petroleum ether. After drying, 859 mg (94%) of compound 2 are obtained in the form of white crystals.

Workup

  1. customDuring the cooling, the quinolone 2 precipitates out in the reaction medium
  2. filtrationThis product is collected by filtration
  3. washrinsed with petroleum ether
  4. customAfter drying

Sources & evidence

ORD record
ord-cec874f104ed4cc181b71e245fcc06f4
Source dataset
uspto-grants-2003_11
Patent number
US06645983B1

Reaction notes

Loading…