Sodium Hydroxide → HCID 59726065, compound

To a stirred solution of aniline 2-3 (11.5 g, 460 mmol) in methanol (250 mL) and H2O (70 mL) was added 2N NaOH (25 mL). The reaction mixture was heated under reflux for 1 h, more 2N NaOH (25 mL) was added and the mixture was heated under reflux for a further 1 h. The solution was cooled and methanol was removed in vacuo. The mixture was dissolved in H2O and extracted with ethyl acetate. The aqueous layer was acidified to pH 2 with conc. HCl. and then extracted into ethyl acetate (×3). The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated to provide the acid 2-4 as a beige solid (10.4 g, 95% yield). 1H NMR (MeOD, 400 MHz) δ 3.80 (s, 3H), 6.70 (s, 1H).

1. temperatureThe reaction mixture was heated
2. temperatureunder reflux for 1 h
3. temperaturethe mixture was heated
4. temperatureunder reflux for a further 1 h
5. temperatureThe solution was cooled
6. custommethanol was removed in vacuo
7. dissolutionThe mixture was dissolved in H2O
8. extractionextracted with ethyl acetate
9. extractionand then extracted into ethyl acetate (×3)
10. washThe combined extracts were washed with brine
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated

ORD record

ord-8e478df49ec4447e927c7371d82b32c9

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889695B2