4-Methoxyphenol → HCID 12675966, compound

HRID 2072245Notes

Reaction equation

HRID 2072245 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.Cl[C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.COC1C=CC(C2C=CC3C(=CC=CC=3)N=2)=CC=1>CN(C)C=O.COCCOC>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 90154-MethoxyphenolHCID 119282-ChloroquinolineHCID 24758Sodium hydrideHCID 1481967HCID 1481967, compound

Product 1

HCID 12675966HCID 12675966, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
5 °C

Procedure

To a stirred suspension of 32 g. sodium hydride (52% suspension in mineral oil) in 475 ml. dimethylformamide and 475 ml. 1,2-dimethoxyethane was added, portionwise during about fifteen minutes, 59.5 g. 4-methoxyphenol followed by, after five minutes, a solution of 95.5 g. 2-chloroquinoline in 130 ml. dimethyl formamide in one portion and the resulting mixture was heated under reflux for sixteen hours, cooled to 5° C., poured into 4000 ml. ice-water and extracted with ether. The ether extract was washed with ice cold 2% aqueous sodium hydroxide solution, water and saturated salt solution, dried and evaporated to dryness under reduced pressure. The resulting crystals were recrystallized from benzene-hexane to give 104 g. 2-(4-methoxyphenyl)quinoline; m.p. 96.5°-98° C.

Workup

  1. additionTo a stirred suspension of 32 g
  2. customafter five minutes
  3. temperatureunder reflux for sixteen hours
  4. additionpoured into 4000 ml
  5. extractionice-water and extracted with ether
  6. extractionThe ether extract
  7. washwas washed with ice cold 2% aqueous sodium hydroxide solution, water and saturated salt solution
  8. customdried
  9. customevaporated to dryness under reduced pressure
  10. customThe resulting crystals were recrystallized from benzene-hexane
  11. customto give 104 g

Sources & evidence

ORD record
ord-f47e99a1a1154d1e90caf59aca405531
Source dataset
uspto-grants-1977_09
Patent number
US04049715

Reaction notes

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