HCID 15550516, compound → HCID 15550517, compound

HRID 1386630Notes

Reaction equation

HRID 1386630 reaction equation
[CH3:1][C:2]1[C:10]([C:11](=[O:24])[C:12](C(OC)=O)([CH3:19])[CH2:13][C:14]([O:16]CC)=[O:15])=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1>Br>[CH3:1][C:2]1[C:10]([C:11](=[O:24])[CH:12]([CH3:19])[CH2:13][C:14]([OH:16])=[O:15])=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

3

Reactant 1

HCID 15550516HCID 15550516, compound

Product 1

HCID 15550517HCID 15550517, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

The compound (4.63 g) of Example 9 was dissolved into 47% hydrobromic acid (50 ml) and the solution was refluxed for 1 hour under heat. This was poured into ice water and extracted with methylene chloride. After the organic layer was dried over anhydrous sodium sulfate, solvent was distilled off under reduced pressure. The residue was purified by means of silica gel column chromatography (developing solvent, methylene chloride:ethanol=10:1) to obtain aimed product (2.76 g) as purple powder.

Workup

  1. temperaturethe solution was refluxed for 1 hour
  2. temperatureunder heat
  3. extractionextracted with methylene chloride
  4. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate, solvent
  5. distillationwas distilled off under reduced pressure
  6. customThe residue was purified by means of silica gel column chromatography (developing solvent, methylene chloride:ethanol=10:1)

Sources & evidence

ORD record
ord-e204c74c6ee8491f98ae4a4f2336d4b2
Source dataset
uspto-grants-2001_07
Patent number
US06265577B1

Reaction notes

Loading…