3-Nitroaniline → HCID 68419705, compound

To a solution of 3-(1-cyano-1-methylethyl)benzoic acid (7.85 g, 41.5 mmol) in tetrahydrofuran (80 mL) were added N,N-dimethylformamide (50 μL) and oxalyl chloride (4.33 mL, 49.8 mmol), and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was concentrated under reduced pressure to give 3-(cyano-1-methylethyl)benzoyl chloride as a pale-brown oil. To a solution of 3-nitroaniline (5.73 g, 41.5 mmol) and N,N-dimethylpyridine-4-amine (253 mg, 2.07 mmol) in pyridine (50 mL) was added dropwise a suspension of 3-(cyano-1-methylethyl)benzoyl chloride in pyridine (30 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and to the residue was added saturated aqueous sodium hydrogen carbonate solution (150 mL), and the mixture was extracted with ethyl acetate (200 mL, 50 mL). The combined organic layer was washed with saturated brine (30 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with ethyl acetate/hexane mixture to give the title compound (11.46 g, 89%) as a pale-yellow solid.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionto the residue was added saturated aqueous sodium hydrogen carbonate solution (150 mL)
3. extractionthe mixture was extracted with ethyl acetate (200 mL, 50 mL)
4. washThe combined organic layer was washed with saturated brine (30 mL)
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationThe insoluble material was filtered off
7. concentrationthe filtrate was concentrated under reduced pressure
8. washThe obtained residue was washed with ethyl acetate/hexane mixture

ORD record

ord-699591d05491481da7a848f5e6c44f68

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344135B2