Epichlorohydrin → 6-Chloro-7-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril

HRID 621552Notes

Reaction equation

HRID 621552 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[NH:8][C:7](=[O:13])[CH2:6][CH2:5]2.[OH-].[Na+].[CH2:16]([CH:18]1[O:20][CH2:19]1)Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:16][CH:18]1[O:20][CH2:19]1)[NH:8][C:7](=[O:13])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium Hydroxide2×HCID 128994206-Chloro-7-hydroxy-3,4-dihydrocarbostyril

Product 1

HCID 128994376-Chloro-7-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20.0 grams of 6-chloro-7-hydroxy-3,4-dihydrocarbostyril and 3.7 g of sodium hydroxide are mixed with 100 ml of methanol and stirred for 3 hours, then 150 ml of epichlorohydrin is added thereto and heated for 5 hours under refluxing conditions. After the reaction is completed, the reaction mixture is concentrated under reduced pressure to dryness. The residue thus obtained is mixed with 100 ml of 2N-sodium hydroxide and stirred well. The insoluble matter is separated by filtration, washed with water and dried. The crude crystals thus obtained are recrystallized from methanol-ethanol to obtain 19.7 g of 6-chloro-7-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril in the form of colorless crystals with a melting point of 190°-192° C.

Workup

  1. temperatureheated for 5 hours under refluxing conditions
  2. concentrationthe reaction mixture is concentrated under reduced pressure to dryness
  3. customThe residue thus obtained
  4. stirringstirred well
  5. customThe insoluble matter is separated by filtration
  6. washwashed with water
  7. customdried
  8. customThe crude crystals thus obtained
  9. customare recrystallized from methanol-ethanol

Sources & evidence

ORD record
ord-d807fc37cef644d8b02f38085e388b01
Source dataset
uspto-grants-1989_04
Patent number
US04824840

Reaction notes

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