Tetrahydrofuran → HCID 19844730, compound

HRID 2351870Notes

Reaction equation

HRID 2351870 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Cl.Cl[CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1.[OH-].[Na+].C1COCC1>CN(C=O)C.O>[N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:24]=[CH:25][C:16]=1[CH2:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][C:9]#[N:10])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 14750504HCID 14750504, compound

Product 1

HCID 19844730HCID 19844730, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.93 g (0.018 mol) 3-(4-hydroxyphenoxy)propionitrile, 3.2 g (0.18 mol) 2-chlormethylquinoline hydrochloride and 18 ml (2N, NaOH) in 25 ml DMF and 25 ml THF is heated over a steam bath for a period of 24 hours. The reaction mixture is poured into water and extracted with ether. The ether extract is washed with water, dried over MgSO4 and concentrated to dryness under reduced pressure. The residue is passed through a silica gel column using hexane/ethyl acetate (3:1) as eluent to obtain the desired product which is used directly in the next step.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washis washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-783eeef1ab354bffad4dcb1855e47089
Source dataset
uspto-grants-1989_10
Patent number
US04874769

Reaction notes

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