HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

2-(Chloromethyl)quinoline → 4,5-Dihydro-5-[3-[(2-quinolinyl)methoxy]phenyl]-2-(2-pyridyl)-1,3-oxazole

HRID 2119049
Notes
Print preview

Reaction equation

HRID 2119049 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1.C[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[CH:30][C:21]=1[CH2:20][O:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 203942-(Chloromethyl)quinolineHCID 10942334Sodium MethoxideHCID 139142643-[2-(Pyridin-2-yl)-4,5-dihydro-1,3-oxazol-5-yl]phenol

Product 1

HCID 139142654,5-Dihydro-5-[3-[(2-quinolinyl)methoxy]phenyl]-2-(2-pyridyl)-1,3-oxazoleYield 21.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4,5-dihydro-5-(3-hydroxyphenyl)-2-(2-pyridyl)-1,3-oxazole (7.3 g, 0.03 mol) and 2-(chloromethyl)quinoline (5.4 g, 0.03 mol) in dimethylformamide (200 ml) is heated to 90° for 16 hours in the presence of sodium methoxide (1.6 g, 0.03 mol). The mixture is dissolved in ethyl acetate and water. The aqueous layer is extracted twice with ethyl acetate. The combined ethyl acetate solutions are washed twice with dilute aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated to obtain an oil. This material is chromatographed on a Water Prep Pak 500 silica column with methylene chloride/methanol 99/1 (v/v) as mobile phase to obtain 2.5 g of purified material as a viscous oil.

Workup

  1. extractionThe aqueous layer is extracted twice with ethyl acetate
  2. washThe combined ethyl acetate solutions are washed twice with dilute aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto obtain an oil
  6. customThis material is chromatographed on a Water Prep Pak 500 silica column with methylene chloride/methanol 99/1 (v/v) as mobile phase

Sources & evidence

ORD record
ord-4fd93a3f2d84459683986ca17bb289ff
Source dataset
uspto-grants-1987_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04681940

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes