Methyl 4-aminobenzoate → HCID 821139, compound

Formic acid (90.0 mL) was added to a dichloromethane solution (900 mL) of methyl 4-aminobenzoate (90.0 g) and to the mixture was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (114 g) at 5° C. over thirty minutes, and then the mixture was stirred at room temperature for three hours. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution (1.2 L) and the pH was adjusted to 10 with 1N sodium hydroxide, and the residue was separated. The aqueous layer was extracted with dichloromethane, and the organic layer was combined and washed with 1N hydrochloric acid, water and brine successively. After the organic layer was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the residue obtained was washed with ethyl acetate to obtain the titled compound (88.7 g) as crystals.

1. customthe residue was separated
2. extractionThe aqueous layer was extracted with dichloromethane
3. washwashed with 1N hydrochloric acid, water and brine successively
4. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
5. customthe solvent was removed under reduced pressure
6. customthe residue obtained
7. washwas washed with ethyl acetate

ORD record

ord-6fe58400623045188e09482df3c63b73

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06956046B2