Dimethylformamide → HCID 66937089, compound

Temperature

100 °C

A mixture of 5-chloro-2-nitro-4-trifluoromethoxy-phenylamine (2.00 g, 7.80 mmol), sodium dithionite (7.06 g, 40.5 mmol), trimethyl orthoformate (23.1 mL, 210 mmol), DMF (23 mL), and acetic acid (4.0 mL) was heated in a sealed tube for 15 h at 100° C. The reaction mixture was cooled to 23° C. and partitioned between EtOAc (100 mL) and saturated aq. NaHCO3 (100 mL). The organic layer was collected and the aqueous layer was extracted with EtOAc (2×80 mL). The combined organic layers were dried, filtered, and concentrated under reduced pressure. The residue was purified (FCC) (0-15% MeOH/DCM) to yield the titled compound (1.46 g, 78%). MS (ESI/CI): mass calcd. for C8H4ClF3N2O, 236.0; m/z found, 237.0 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.11 (5, 1H), 7.74 (s, 1H), 7.64 (s, 1H).

1. temperatureThe reaction mixture was cooled to 23° C.
2. custompartitioned between EtOAc (100 mL) and saturated aq. NaHCO3 (100 mL)
3. customThe organic layer was collected
4. extractionthe aqueous layer was extracted with EtOAc (2×80 mL)
5. customThe combined organic layers were dried
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified (FCC) (0-15% MeOH/DCM)

ORD record

ord-9304c56389a8430e967c24926ffbcba5

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759345B2