Bromine → HCID 15485485, compound

HRID 369426Notes

Reaction equation

HRID 369426 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:32])=[C:8]([CH:31]=1)[C:9](=[O:30])[CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)=[CH:14][CH:13]=1)([OH:3])=[O:2].[Br:33]Br>C(O)(=O)C>[Br:33][C:6]1[CH:5]=[C:4]([C:1]([OH:3])=[O:2])[CH:31]=[C:8]2[C:7]=1[O:32][C:11]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)=[CH:16][CH:17]=1)=[CH:10][C:9]2=[O:30]

Participants

4

Reactant 2

HCID 24408BromineHCID 54200226HCID 54200226, compound

Product 1

HCID 15485485HCID 15485485, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a solution of 5'-carboxy-2'-hydroxy-4-(2-quinolinylmethoxy)chalcone (1 mmol) in 10 ml of glacial acetic acid, 0.06 ml of bromine was gradually added dropwise. The reaction mixture was stirred at room temperature for 3 hours, and the resulting yellow precipitate was collected and then washed with water. The precipitate was next dissolved in a mixed solvent which was consisted of 8 ml of ethanol and 15 ml of 6% potassium hydroxide. The resulting solution was stirred further for 4 hours. After the reaction mixture was acidified, the resulting precipitate was collected by filtration and then recrystallized from DMF, whereby the title compound represented by the following formula was obtained (yield: 25%). ##STR16##

Workup

  1. customthe resulting yellow precipitate was collected
  2. washwashed with water
  3. dissolutionThe precipitate was next dissolved in a mixed solvent which
  4. stirringThe resulting solution was stirred further for 4 hours
  5. filtrationthe resulting precipitate was collected by filtration
  6. customrecrystallized from DMF, whereby the title compound
  7. customwas obtained (yield: 25%)

Sources & evidence

ORD record
ord-3f11124274264c429add157dbc6004c6
Source dataset
uspto-grants-2000_10
Patent number
US06136848

Reaction notes

Loading…