Sulfuric Acid → 6-Aminomethyl-3,4-diethoxy-2-fluorobenzonitrile sulfate

Temperatur

-22 °C

A mixture of 4,5-diethoxy-3-fluorophthalonitrile (2.34 g, 10 mol) prepared in Preparation Example 1, sulfuric acid (0.56 mL, 10 mol), 20% palladium hydroxide-carbon (0.59 g, 50% hydrate) (20% palladium-carbon powder, palladium hydroxide type (hydrate), N.E. Chemical Corporation) and 1,2-dimethoxyethane (23 mL) was stirred at −22° C. under hydrogen atmosphere (atmospheric pressure) for 24 hours. After insoluble matter in the reaction mixture was filtered off, the residue was washed with methanol (23 mL) and the combined filtrate was divided into five equal portions. After one of them was concentrated at room temperature under reduced pressure, 1,2-dimethoxyethane (9.2 mL) was added thereto, and the mixture was stirred. Then, triethylamine (0.56 mL, 4 mol) was added dropwise thereto and the mixture was stirred at room temperature for one hour. Precipitated crystals were filtered, washed with a 5% methanol-1,2-dimethoxyethane solution, and dried at room temperature under reduced pressure to give 0.59 g of the ½ triethylamine solvate of the title compound (yield: 76%) as dark white crystals.

1. filtrationAfter insoluble matter in the reaction mixture was filtered off
2. washthe residue was washed with methanol (23 mL)
3. concentrationAfter one of them was concentrated at room temperature under reduced pressure, 1,2-dimethoxyethane (9.2 mL)
4. additionwas added
5. stirringthe mixture was stirred
6. stirringthe mixture was stirred at room temperature for one hour
7. customPrecipitated crystals
8. filtrationwere filtered
9. washwashed with a 5% methanol-1,2-dimethoxyethane solution
10. customdried at room temperature under reduced pressure

ORD-Eintrag

ord-2f06102da0fb45d8831890ff6feb0c55

Quelldatensatz

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07585982B2