Hydrogen Bromide → HCID 86707478, compound

HRID 338959Notes

Reaction equation

HRID 338959 reaction equation
[CH:1]1([C:4]2[C:5]([O:15]C)=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[C:11]([CH3:14])[CH:10]=[CH:9]3)[CH2:3][CH2:2]1.Br.[OH-].[NH4+]>>[CH3:14][C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[C:4]3[CH2:1][CH:2]([CH3:3])[O:15][C:5]3=[CH:6][CH:7]=2)[N:12]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 14923Ammonium HydroxideHCID 70983792HCID 70983792, compound

Product 1

HCID 86707478HCID 86707478, compoundYield 79%

Procedure

A solution of 8-cyclopropyl-7-methoxy-2-methylquinoline (0.53 g, 2.5 mmol) in hydrobromic acid (48%; 9.9 mL, 2.5 mmol) was heated at reflux for 3 days. After cooling, the reaction mixture was neutralized to pH 8 by addition of ammonium hydroxide and extracted with dichloromethane (3×20 mL). The combined organic extracts were washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by reverse phase chromatography on C18 (0-100% acetonitrile/water) afforded the title compound (0.39 g, 79%).

Workup

  1. temperatureat reflux for 3 days
  2. temperatureAfter cooling
  3. extractionextracted with dichloromethane (3×20 mL)
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by reverse phase chromatography on C18 (0-100% acetonitrile/water)

Sources & evidence

ORD record
ord-7529832b548e42cb9dda2dc1a17910dd
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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