Acetic Acid → 3-Amino-7-bromoquinoline-2-carboxylic acid

Temperature

50 °C

To a mixture of ethyl 3-amino-7-bromoquinoline-2-carboxylate (Ark Pharm, 113.9 mg, 0.3859 mmol) and lithium hydroxide monohydrate (82.8 mg, 1.97 mmol), THF (2.50 mL) was added, followed by water (0.50 mL). The resulting mixture was stirred at 50° C. for 2 h. The reaction mixture was then cooled to room temperature and water (25 mL) was then added, followed by AcOH (245.9 mg, 4.095 mmol) to adjust the pH to 5. The mixture was extracted with EtOAc (3×25 mL). The combined organic extract was washed with brine (50 mL), then dried over Na2SO4, and concentrated to yield a yellow solid (83.3 mg). The crude product was used directly in the next step without further purification. LCMS calc. for C10H8BrN2O2(M+H)+: m/z=267.0. found 267.0.

1. additionwas added
2. temperatureThe reaction mixture was then cooled to room temperature
3. extractionThe mixture was extracted with EtOAc (3×25 mL)
4. extractionThe combined organic extract
5. washwas washed with brine (50 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated

ORD record

ord-8a5d4fab190f416587de20e4fb3a380b

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278950B2