Potassium Iodide → HCID 14349145, compound

HRID 414852Notes

Reaction equation

HRID 414852 reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH2:13]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:28]1[CH:29]=[C:30]([OH:34])[CH:31]=[CH:32][CH:33]=1)[OH:27])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH2:13]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:28]1[CH:29]=[C:30]([CH:31]=[CH:32][CH:33]=1)[O:34][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[OH:27])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 21280520HCID 21280520, compound

Product 1

HCID 14349145HCID 14349145, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Chloromethyl quinoline (3.6 g) was refluxed with 3-(6-benzyloxy-1-hydroxyhexyl)phenol (4.2 g), powdered potassium carbonate (8 g) and potassium iodide (0.2 g) in dry acetone (150 ml) overnight (16 hrs.). The suspension was filtered, the filtrate was concentrated in vacuo and then taken up in ethyl acetate. This solution was washed with 5% NaOH solution, water and brine and then dried. All solvent was removed to obtain the crude product which was purified by chromatography (silica gel; 30% ethyl acetate in hexanes). The pure compound was dissolved in ether, and was precipitated as the hydrochloride salt with a dry ethereal solution of HCl. The pure salt was filtered, washed with cold water, and dried in vacuo to yield a tan powder (1.5 g), mp 86°-89° C.

Workup

  1. filtrationThe suspension was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. washThis solution was washed with 5% NaOH solution, water and brine
  4. customdried
  5. customAll solvent was removed
  6. customto obtain the crude product which
  7. customwas purified by chromatography (silica gel; 30% ethyl acetate in hexanes)
  8. dissolutionThe pure compound was dissolved in ether
  9. customwas precipitated as the hydrochloride salt with a dry ethereal solution of HCl
  10. filtrationThe pure salt was filtered
  11. washwashed with cold water
  12. customdried in vacuo

Sources & evidence

ORD record
ord-5ee3acaa41414f67ada9a330296cc757
Source dataset
uspto-grants-1988_12
Patent number
US04794188

Reaction notes

Loading…