Bromine → HCID 131712131, compound

HRID 127710Notes

Reaction equation

HRID 127710 reaction equation
[Br:1]Br.[NH:3]1[C:13]2[CH2:12][CH2:11][CH2:10][C:9](=[O:14])[C:8]=2[CH2:7][CH2:6][C:4]1=[O:5]>C(Cl)(Cl)(Cl)Cl>[Br:1][CH:6]1[CH2:7][C:8]2[C:9](=[O:14])[CH2:10][CH2:11][CH2:12][C:13]=2[NH:3][C:4]1=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 2936414,6,7,8-Tetrahydro-2,5(1H,3H)-quinolinedione

Product 1

HCID 131712131HCID 131712131, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of 3.6 g of bromine in 50 ml of carbon tetrachloride was added, while stirring under ice-cooling, to a solution of 4.0 g of 3,4,5,6,7,8-hexahydrocarbostyril-5-one in 50 ml of carbon tetrachloride. After allowing the mixture to stand for one minute, the precipitate formed was removed by decantation. The carbon tetrachloride layer was distilled at room temperature to remove the solvent (CCl4), and the resulting crystals were combined with the above precipitate followed by being washed with acetone to give quantitatively 8-(or 6-) bromo-3,4,5,6,7,8-hexahydrocarbostyril-5-one having a melting point of 126°-127° C. as yellow crystals. The thus obtained crystals were dissolved in 80 ml of carbon tetrachloride, and 3.0 g of 3-chloro-1,2-propanediol and 1.5 g of 2,4,6-tribromophenol were added to the solution. The mixture was heated at reflux for 2 hours and thereafter worked up in the same manner as described in Example 6 to give 2.1 g of 5-(2-hydroxy- 3-chloro)propoxy-3,4-dihydrocarbostyril having a melting point of 157°-158° C. as colorless amorphous crystals.

Workup

  1. customthe precipitate formed
  2. customwas removed by decantation
  3. distillationThe carbon tetrachloride layer was distilled at room temperature
  4. customto remove the solvent (CCl4)
  5. washby being washed with acetone

Sources & evidence

ORD record
ord-a90c2e9fa9904a75b3e8f295dd192d8a
Source dataset
uspto-grants-1981_03
Patent number
US04256890

Reaction notes

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