Sodium Iodide → HCID 14422686, compound

HRID 610361Notes

Reaction equation

HRID 610361 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2=[O:12].Cl[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O.C(Cl)Cl.CC(C)=O>[N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[CH2:14][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2=[O:12]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 70989446-Hydroxy-chroman-4-one

Product 1

HCID 14422686HCID 14422686, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

A mixture of 6-hydroxy-4-chromanone (10.0 g, 0.0609 mol), 2-chloromethylquinoline (11.9 g, 0.0670 mol), sodium iodide (10.0 g, 0.0670 mol), potassium carbonate (25.3 g, 0.183 mol), and acetone (200 ml) was refluxed overnight under N2 atmosphere. After 17 hours the reaction appeared lighter and tlc analysis (10% EtOAc/CH2Cl2) indicated complete conversion of starting material to a slightly less polar products The mixture was cooled, filtered, and the filtrate concentrated in vacuo. The residue was taken up in ethyl acetate (400 ml), washed with H2O and brine, dried over MgSO4, and concentrated in vacuo to a dark brown oil. Purification on a silica gel column eluted with 10% ethyl acetate/CH2Cl2 gave title product as an off-white solid, 15.3 g (82%), m.p. 112-114° C.; tlc (1:9 ethyl acetate:CH2Cl2) Rf 0.30.

Workup

  1. temperaturewas refluxed overnight under N2 atmosphere
  2. temperaturewas cooled
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. washwashed with H2O and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo to a dark brown oil
  8. customPurification on a silica gel column
  9. washeluted with 10% ethyl acetate/CH2Cl2

Sources & evidence

ORD record
ord-596d6ea75c7b4d4db436c7876fa06a7f
Source dataset
uspto-grants-1999_12
Patent number
US05998451

Reaction notes

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