Ethanol → HCID 53416444, compound

Temperature

50 °C

Iron powder (37.42 g, 670 mmol) was added in small portions to a stirred suspension of finely grinded 5-methyl-2-nitro-4-trifluoromethyl-benzonitrile from step 3 (34.58 g, 150 mmol) in methanol (75 mL) and 37% HCl (93 mL). The internal temperature was kept between 40 and 60° C. by external water bath cooling. The resulting brown solution was stirred for 1 h at 50° C., giving a green suspension. The mixture was poured into ice cold water (600 mL), the precipitated solid was filtered off and washed with water to give a green solid, which was dissolved in boiling ethanol (700 mL), activated carbon (ca. 10 g) was added, and the mixture was refluxed for 1 h. The hot solution was filtered, and the solvent was evaporated in vacuum to leave the title compound as a brown-yellow solid (23.55 g, 78%), which was used without further purification. MS (EI) 200.1 [M].

1. customThe internal temperature was kept between 40 and 60° C. by external water bath
2. temperaturecooling
3. customgiving a green suspension
4. filtrationthe precipitated solid was filtered off
5. washwashed with water
6. customto give a green solid, which
7. dissolutionwas dissolved
8. additionwas added
9. temperaturethe mixture was refluxed for 1 h
10. filtrationThe hot solution was filtered
11. customthe solvent was evaporated in vacuum

ORD record

ord-53a292301d734c7f8eff4318808d4707

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063048B2