Sodium Carbonate → HCID 54489064, compound

HRID 615644Notes

Reaction equation

HRID 615644 reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2.C([O-])(=O)C.[Na+].[C:19]([O:24][CH2:25][CH2:26][OH:27])(=[O:23])[C:20]([CH3:22])=[CH2:21].C(=O)([O-])[O-].[Na+].[Na+]>O>[C:19]([O:24][CH2:25][CH2:26][O:27][CH2:2][C:3]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2)(=[O:23])[C:20]([CH3:22])=[CH2:21]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 133602-Hydroxyethyl MethacrylateHCID 4168815-(Chloromethyl)quinolin-8-olHCID 517045Sodium Acetate

Product 1

HCID 54489064HCID 54489064, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Chloromethyl-8-hydroxyquinoline (46 g) (prepared by the method of Kolobielski, J. Heterocyclic Chem. 275, (1966)), sodium acetate (16.4 g) and hydroxyethyl methacrylate (200 ml) were stirred and heated on a steam bath for 5 hours, and the resulting slurry was dissolved in water (1 liter). Solid sodium carbonate was added until alkaline, and then the precipitate was collected, washed with water, dissolved in ether (500 ml), dried with MgSO4, and then treated with HCl gas to precipitate the hydrochloride salt. The latter was collected, washed with ether, air dried, dissolved in water (1 liter), and treated with solid sodium carbonate until alkaline. The resulting precipitate was collected, washed with water, dried, and crystallized from light petroleum (b.p. 60°-80° C.) to give 23 g colorless needles, m.p. 90°-1° C.

Workup

  1. temperatureheated on a steam bath for 5 hours
  2. customthe precipitate was collected
  3. washwashed with water
  4. dissolutiondissolved in ether (500 ml)
  5. dry with materialdried with MgSO4
  6. additiontreated with HCl gas
  7. customto precipitate the hydrochloride salt
  8. customThe latter was collected
  9. washwashed with ether, air
  10. customdried
  11. dissolutiondissolved in water (1 liter)
  12. additiontreated with solid sodium carbonate until alkaline
  13. customThe resulting precipitate was collected
  14. washwashed with water
  15. customdried
  16. customcrystallized from light petroleum (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-2d8a4a6449cd48958b558087ae75b217
Source dataset
uspto-grants-1985_02
Patent number
US04500601

Reaction notes

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