Bromine → HCID 18979081, compound

HRID 2393090Notes

Reaction equation

HRID 2393090 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[C:12]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH:11]=[CH:10]2>CO>[Br:1][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[N:13]2

Participants

4

Reactant 2

HCID 24408BromineHCID 18979075HCID 18979075, compound

Product 1

HCID 18979081HCID 18979081, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Bromine (200 μl) was added in a dropwise manner to a stirred and cooled (0°-5° C.) solution of 8-methoxy-2-(3-pyridyl)quinoline (780 mg) in methanol (30 ml) under a nitrogen atmosphere. The reaction mixture was stirred for 15 minutes then quenched by the addition of 5% aqueous sodium metabisulfite solution (7ml). The reaction mixture was evaporated in vacuo and the residue partitioned between 0.5N sodium hydroxide solution (65 ml) and dichloromethane (75 ml). The aqueous phase was reextracted with dichloromethane (2×75 ml) and the combined organic phases were dried (magnesium sulfate), filtered and evaporated in vacuo. Trituration with diethyl ether afforded the title compound (570 mg) as a pale brown solid.

Workup

  1. stirringThe reaction mixture was stirred for 15 minutes
  2. customthen quenched by the addition of 5% aqueous sodium metabisulfite solution (7ml)
  3. customThe reaction mixture was evaporated in vacuo
  4. customthe residue partitioned between 0.5N sodium hydroxide solution (65 ml) and dichloromethane (75 ml)
  5. dry with materialthe combined organic phases were dried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-16ddcd907db54c0a87ee9f278062755d
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

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