4-Methyl-3-nitrobenzoic acid → 4-(4-Methyl-3-nitrobenzoyl)morpholine

The compound ([5]-(53)-278) (6.5272 g) prepared in Example 72 was dissolved in anhydrous DMF (98 ml). Then, 1-hydroxybenzotriazole (6.3297 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (8.9795 g), triethylamine (6.5 ml), and morpholine (4.1 ml) were added to the solution. The mixture was stirred at room temperature for 4 hours. A small amount of water was added to the resulting yellowish orange solution including the white salt to obtain a homogeneous solution. The solution was concentrated. The residue was dissolved in chloroform, and the solution was washed with 1N HCl aqueous solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and concentrated to obtain yellowish brown crystals (8.9903 g). The product was recrystallized from n-hexane/ethyl acetate to obtain the above-captioned compound ([5]-(54)-278) (7.8455 g) as light yellow crystals.

1. customto obtain a homogeneous solution
2. concentrationThe solution was concentrated
3. dissolutionThe residue was dissolved in chloroform
4. washthe solution was washed with 1N HCl aqueous solution and saturated brine
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
6. concentrationconcentrated

ORD-Eintrag

ord-bca3c40aca0248588a77df99acc2f0b2

Quelldatensatz

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05696118