Trifluoroacetic acid → HCID 86083508, compound

To a solution of 1,1-dimethylethyl (5-chloro-3-ethynyl-2-methylphenyl)carbamate (242 mg, 0.91 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (500 μl). The solution was stirred at ambient temperature for 1 hour. The solution was partitioned between saturated sodium bicarbonate and dichloromethane. The aqueous layer was extracted twice with dichloromethane. The combined organic portions were washed with brine, dried over sodium sulfate, filtered and concentrated in-vacuo to afford an orange oil which was purified by column chromatography (silica gel, 50% dichloromethane in hexane). The product was collected to afford 60 mg, 0.36 mmol (40%) of 5-chloro-3-ethynyl-2-methylaniline as a white solid. 1H NMR (400 MHz, CDCl3): 6.90 (d, 1H), 6.63 (d, 1H), 3.71 (br s, 2H), 3.24 (s, 1H), 2.23 (s, 3H); MS (EI) for C9H8ClN: 166 (MH+).

1. customThe solution was partitioned between saturated sodium bicarbonate and dichloromethane
2. extractionThe aqueous layer was extracted twice with dichloromethane
3. washThe combined organic portions were washed with brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in-vacuo
7. customto afford an orange oil which
8. customwas purified by column chromatography (silica gel, 50% dichloromethane in hexane)
9. customThe product was collected

ORD record

ord-624a8e99308a45d4bd14e41e58e041c9

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07846959B2