Hydrochloric Acid → HCID 136372363, compound

To a mixture of 4-(cyclopropylmethoxy)-2-nitroaniline (416 mg) and ethanol (2 mL) was added 6M hydrochloric acid (1.5 mL), and ethanol was evaporated under reduced pressure. To the obtained suspension was added a mixture of sodium nitrite (145 mg) and water (1 mL) under ice-cooling, and the mixture was stirred for 30 min. A mixture of phenol (245 mg) and 8M aqueous sodium hydroxide solution (1.2 mL) was added thereto, and the mixture was stirred for 1 hr. To the reaction mixture was added 1M hydrochloric acid, and the mixture was extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a dark red solid (187 mg).

1. customwas evaporated under reduced pressure
2. additionTo the obtained suspension was added
3. additiona mixture of sodium nitrite (145 mg) and water (1 mL) under ice-
4. temperaturecooling
5. additionA mixture of phenol (245 mg) and 8M aqueous sodium hydroxide solution (1.2 mL)
6. additionwas added
7. stirringthe mixture was stirred for 1 hr
8. additionTo the reaction mixture was added 1M hydrochloric acid
9. extractionthe mixture was extracted twice with ethyl acetate
10. washThe combined organic layer was washed with saturated brine
11. dry with materialdried over anhydrous magnesium sulfate
12. customthe solvent was evaporated under reduced pressure
13. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-acba2b4c706246dc86ac1e42cb12ff29

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729102B2