Sodium Hydroxide → 2-[3-(3-Cyanopropoxy)phenoxymethyl]quinoline

HRID 1904679Notes

Reaction equation

HRID 1904679 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[OH:14][C:15]1[CH:16]=[C:17]([CH:24]=[CH:25][CH:26]=1)[O:18][CH2:19][CH2:20][CH2:21][C:22]#[N:23].[OH-].[Na+]>CS(C)=O>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:3][O:14][C:15]1[CH:16]=[C:17]([CH:24]=[CH:25][CH:26]=1)[O:18][CH2:19][CH2:20][CH2:21][C:22]#[N:23]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 145017154-(3-Hydroxyphenoxy)butyronitrile

Product 1

HCID 145017112-[3-(3-Cyanopropoxy)phenoxymethyl]quinolineYield 66.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 15.3 g of 2-chloromethylquinoline hydrochloride, 12.6 g of 4-(3-hydroxyphenoxy)butyronitrile and 5.7 g of sodium hydroxide was stirred with 80 ml of dimethylsulfoxide at room temperature for 4 hours. The reaction mixture was partitioned between water and ether. The ether extract was evaporated to yield 23.9 g, of crude product. Crystallization from ethyl acetate:hexane and then from ethanol:hexane gave 15 g of grey needles, m.p. 84°-85° C.

Workup

  1. customThe reaction mixture was partitioned between water and ether
  2. extractionThe ether extract
  3. customwas evaporated
  4. customto yield 23.9 g
  5. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-2952eaece6cb43ab94ffd26607fde88a
Source dataset
uspto-grants-1989_06
Patent number
US04839369

Reaction notes

Loading…