1-Bromo-3-chloropropane → HCID 12899443, compound

HRID 569953Notes

Reaction equation

HRID 569953 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:13])[C:11]=1[OH:12])[NH:8][C:7](=[O:14])[CH2:6][CH2:5]2.[OH-].[Na+].Br[CH2:18][CH2:19][CH2:20][Cl:21]>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:13])[C:11]=1[O:12][CH2:18][CH2:19][CH2:20][Cl:21])[NH:8][C:7](=[O:14])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 21243036HCID 21243036, compound

Product 1

HCID 12899443HCID 12899443, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5 Grams of 6-chloro-8-bromo-7-hydroxy-3,4-dihydrocarbostyril and 3 g of sodium hydroxide are mixed with 120 ml of isopropanol and stirred at 50°-60° C. for 1 hour. Then 10 ml of 3-bromo-1-chloropropane are added thereto and stirred at 70°-80° C. for 6 hours. The reaction mixture is concentrated under reduced pressure to dryness and the residue thus obtained is extracted with chloroform. The chloroform layer is washed with water and dried. Then chloroform is removed by distillation and the residue thus formed is recrystallized from ethanol to obtain 6.2 g of 6-chloro-8-bromo-7-(3-chloropropoxy)-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with a melting point of 87°-88° C.

Workup

  1. stirringstirred at 70°-80° C. for 6 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure to dryness
  3. customthe residue thus obtained
  4. extractionis extracted with chloroform
  5. washThe chloroform layer is washed with water
  6. customdried
  7. customThen chloroform is removed by distillation
  8. customthe residue thus formed
  9. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-d3ae5a71eb6e421fa307d227187b84c6
Source dataset
uspto-grants-1988_03
Patent number
US04734416

Reaction notes

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