Hydrochloric Acid → HCID 59395032, compound

To a solution of methyl 2-(2,4-dinitrophenyl)-3,3,3-trifluoro-2-hydroxypropanoate (1.3 g, 4.01 mmol) in ethyl acetate (18 mL) was added (pH3) HCl (5.2 mL) followed by 10% Pd/C (350 mg) in ethyl acetate (3 mL). The reaction mixture was stirred overnight under an atmosphere of H2. The reaction mixture was filtered through a pad of Celite and the filtrate was concentrated in vacuo. The crude residue obtained was partitioned between dichloromethane (25 mL) and aqueous saturated NaHCO3 (15 mL). The organic phase was separated and the aqueous phase was extracted dichloromethane (2×25 mL). The combined organic phase was dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography (50-100% ethyl acetate/hexanes) to give 6-amino-3-hydroxy-3-(trifluoromethyl)indolin-2-one (921 mg, 99%)

1. filtrationThe reaction mixture was filtered through a pad of Celite
2. concentrationthe filtrate was concentrated in vacuo
3. customThe crude residue obtained
4. customwas partitioned between dichloromethane (25 mL) and aqueous saturated NaHCO3 (15 mL)
5. customThe organic phase was separated
6. extractionthe aqueous phase was extracted dichloromethane (2×25 mL)
7. dry with materialThe combined organic phase was dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was purified by silica gel column chromatography (50-100% ethyl acetate/hexanes)

ORD record

ord-25d31953b99145969fcdf243f681b9e4

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08614327B2