Propanal → HCID 58639132, compound

200 mg of 1-(4-bromo-2-methylphenyl)hydrazine was suspended in 10.0 mL EtOH propionaldehyde (678 μL) was added. The reaction became clear after the addition of propionaldehyde. The resulting solution was then stirred at room temperature for 45 minutes. The reaction was concentrated and zinc(II)chloride (1070.0 mg) was added and the mixture was heated at 170° C. for 30 minutes. The melting mixture was then cooled to room temperature, and diluted with 10% HCl solution. The solution was then extracted with dichloromethane, dried over magnesium sulfate, filtered and concentrated. The residue was flash chromatographed (0-10% EtOAc/Haptanes gradient) to obtain 317.0 mg of 5-bromo-3,7-dimethyl-1H-indole. LC-MS @ 222.1 (M−1)

1. additionwas added
2. concentrationThe reaction was concentrated
3. additionzinc(II)chloride (1070.0 mg) was added
4. temperaturethe mixture was heated at 170° C. for 30 minutes
5. temperatureThe melting mixture was then cooled to room temperature
6. additiondiluted with 10% HCl solution
7. extractionThe solution was then extracted with dichloromethane
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customchromatographed (0-10% EtOAc/Haptanes gradient)

ORD record

ord-d1ea2281dec145849de4fb4f1ce3b329

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318762B2