Propanal → HCID 58639132, compound

HRID 1880398Notes

Reaction equation

HRID 1880398 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]N)=[C:4]([CH3:10])[CH:3]=1.[CH:11](=O)[CH2:12][CH3:13]>C(O)C.Cl.[Cl-].[Cl-].[Zn+2]>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([CH3:10])[CH:3]=1)[NH:8][CH:11]=[C:12]2[CH3:13]

Participants

6

Reactant 2

HCID 527PropanalHCID 3722075(4-bromo-2-methylphenyl)hydrazine

Product 1

HCID 58639132HCID 58639132, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a suspenstion of (4-bromo-2-methylphenyl)hydrazine (1.44 g, 7.16 mmol) in ethanol (10 mL) was added propionaldehyde (0.68 mL, 9.3 mmol). The solution became clear and the mixture was stirred at room temperature for 45 minutes. The solvents were removed and anhydrous ZnCl2 (1.07 g, 7.88 mmol) was added and the mixture was heated at 170° C. for 30 minutes. The mixture was cooled to room temperature, diluted with 10% HCl, extracted with CH2Cl2 and the organic extract was dried over MgSO4. After filtration and concentration, the residue was purified by CombiFlash (0-10% EtOAc/heptane) to provide 5-bromo-3,7-dimethyl-1H-indole (317 mg, 20%).

Workup

  1. customThe solvents were removed
  2. temperaturethe mixture was heated at 170° C. for 30 minutes
  3. temperatureThe mixture was cooled to room temperature
  4. extractionextracted with CH2Cl2
  5. extractionthe organic extract
  6. dry with materialwas dried over MgSO4
  7. filtrationAfter filtration and concentration
  8. customthe residue was purified by CombiFlash (0-10% EtOAc/heptane)

Sources & evidence

ORD record
ord-7295959063304c5ab5e9497826368c9b
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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