7-Aminoquinoline → HCID 22462229, compound

HRID 1936588Notes

Reaction equation

HRID 1936588 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[Br:17]Br>C(O)(=O)C>[NH2:1][C:2]1[C:11]([Br:17])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 113777-AminoquinolineHCID 24408BromineHCID 517045Sodium Acetate

Product 1

HCID 22462229HCID 22462229, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 401 mg of 7-aminoquinoline in 15 mL of glacial acetic acid are added 913 mg of sodium acetate followed by a solution of 0.14 mL of bromine in 15 mL of glacial acetic acid. The resulting yellow slurry is stirred at room temperature for 2 hours. The brown mixture is rotary evaporated and the residue is diluted with water and ethyl acetate. The mixture is basified using 1 N sodium hydroxide and decanted. The organic layer is washed with water followed by brine. The combined aqueous layers are extracted with ethyl acetate; the combined organic layers are dried over magnesium sulfate and rotary evaporated. The residue is purified by flash column chromatography on silica gel, eluting with 20% to 50% ethyl acetate/hexanes followed by recrystallization from hexanes/methylene chloride to provide 521 mg of 7-amino-8-bromoquinoline as a pale brown solid.

Workup

  1. customThe brown mixture is rotary evaporated
  2. additionthe residue is diluted with water and ethyl acetate
  3. customdecanted
  4. washThe organic layer is washed with water
  5. extractionThe combined aqueous layers are extracted with ethyl acetate
  6. dry with materialthe combined organic layers are dried over magnesium sulfate and rotary evaporated
  7. customThe residue is purified by flash column chromatography on silica gel
  8. washeluting with 20% to 50% ethyl acetate/hexanes
  9. customfollowed by recrystallization from hexanes/methylene chloride

Sources & evidence

ORD record
ord-cd7b8dc1dfbf47b0b456538e34abd160
Source dataset
uspto-grants-2002_05
Patent number
US06391878B2

Reaction notes

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