Acetic Acid → HCID 89690464, compound

Temperature

75 °C

In a 500 ml round bottom flask equipped with a magnetic stir bar, the iron powder (5.59 g, 100.15 mmol) was suspended in clean, dry, reagent-grade ethanol (300.00 ml, 5138.06 mmol) and the mixture was stirred vigorously under nitrogen at room temperature. To this was added the acetic acid (30.00 ml, 524.05 mmol) and the reaction was allowed to stir for 5 min before the 2-chloro-5-nitro-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid 1d (1.51 g, 4.01 mmol) was added in one portion. The reaction was then warmed to 75° C. and allowed to stir overnight. The reaction was cooled to room temperature and was then filtered through Celite, washing heavily with methanol. The deep red product solution was then concentrated under reduced pressure and the resultant ruby red oil was taken up in 200 ml of ethyl acetate. To this solution was added 200 ml of saturated NaHCO3 (aq) solution and the layers were then separated and the product was extracted out of the aqueous using ethyl acetate (3×100 ml). The organic phases were then combined and washed with brine (1×200 ml) and dried over Na2SO4. The solution was then decanted and the solvent was removed under reduced pressure. The crude product, 5-amino-2-chloro-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid 14a (1.22 g, 3.53 mmol), was isolated as a brown solid and was carried on without further purification. LCMS=346 (M+H).

1. customIn a 500 ml round bottom flask equipped with a magnetic stir bar
2. customdry
3. additionwas added in one portion
4. temperatureThe reaction was cooled to room temperature
5. filtrationwas then filtered through Celite
6. washwashing heavily with methanol
7. concentrationThe deep red product solution was then concentrated under reduced pressure
8. additionTo this solution was added 200 ml of saturated NaHCO3 (aq) solution
9. customthe layers were then separated
10. extractionthe product was extracted out of the
11. washwashed with brine (1×200 ml)
12. dry with materialdried over Na2SO4
13. customThe solution was then decanted
14. customthe solvent was removed under reduced pressure

ORD record

ord-068f8c41acdc41c2967694f94de27f8d

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409897B2