Sodium Iodide → HCID 21898097, compound

HRID 719394Notes

Reaction equation

HRID 719394 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)=[CH2:2].Cl[CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[C:14]([CH3:22])[CH:13]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Na+].[I-]>CS(C)=O>[CH3:22][C:14]1[CH:13]=[C:12]([CH2:11][O:9][C:6]2[CH:7]=[CH:8][C:3]([CH:1]=[CH2:2])=[CH:4][CH:5]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 624534-VinylphenolHCID 115357194-(Chloromethyl)-2-methylquinoline

Product 1

HCID 21898097HCID 21898097, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-vinylphenol (10% wt. solution in propylene glycol) (1.25 g, 1.04 mmol), 4-Chloromethyl-2-methylquinoline (0.24 g, 1.2 eq), Cs2CO3 (0.85 g, 2.5 eq) and NaI (0.20 g, 1.2 eq) in DMSO (1 ml) was stirred at rt overnight. After work up, the residue was purified by flash column chromatography (40% ethyl acetate-hexanes) to give 2-methyl-4-(4-vinyl-phenoxymethyl)-quinoline (0.134 g, 46.8%) as a white solid. MS Found: (M+H)+=276.

Workup

  1. customAfter work up, the residue was purified by flash column chromatography (40% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-41a746ecaa204c13a0943f5c9372ee62
Source dataset
uspto-grants-2006_11
Patent number
US07132432B2

Reaction notes

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