Tetrahydrofuran → 3-(2-Methoxyethoxy)quinoline

HRID 863310Notes

Reaction equation

HRID 863310 reaction equation
[H-].[K+].[OH:3][C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2.[O:14]1[CH2:18]C[CH2:16][CH2:15]1>CN(C)C=O>[CH3:18][O:14][CH2:15][CH2:16][O:3][C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 113763-HydroxyquinolineHCID 82127Potassium hydride

Product 1

HCID 539423373-(2-Methoxyethoxy)quinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.75 g of a potassium hydride suspension (20% in oil) is added to a solution of 0.5 g of 3-hydroxyquinoline in 10 ml of tetrahydrofuran, while cooling with ice, and the mixture is stirred for 1 h. 1.25 ml of 2-bromomethyl methyl ether, dissolved in 10 ml of dimethylformamide, are then added and the mixture is allowed to warm to room temperature and is finally stirred at 60° C. for 1 h. After customary working up, the 3-(Methoxyethoxy)quinoline thus obtained is purified by means of FC over 80 g of silica gel (mobile phase B): Rf (97:3:0.5 mixture of methylene chloride, methanol and concentrated ammonia)=0.31. 1.0 g of the quinoline derivative mentioned in 10 ml of ethanol is hydrogenated in the presence of 0.1 g of palladium-on-charocal (10% of Pd) at 50° C. for 4 h. FC over 50 g of silica gel with a 100:1 mixture of methylene chloride and methanol as the eluting agent gives 3(R,S)-methoxyethoxy-1,2,3,4-tetrahydroquinoline: Rf (97:3:0.5 mixture of methylene chloride, methanol and concentrated ammonia)=0.49; MS: M+ =207.

Workup

  1. temperaturewhile cooling with ice
  2. additionare then added
  3. stirringis finally stirred at 60° C. for 1 h

Sources & evidence

ORD record
ord-98e73457e1684130af9ec96cde3f3431
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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