Methyl α-hydroxy-2,4-dinitro-α-(trifluoromethyl)benzeneacetate → 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 successively added pH3HCl (5.2 mL), then PdC (350 mg) in ethyl acetate (3 mL). The mixture was vigorously stirred overnight under H2 (1 atm). The catalyst was filtered off through Celite and the filtrate was concentrated to dryness. The crude residue obtained was partitioned between DCM (25 mL) and aqueous saturated NaHCO3 (15 mL). The organic phase was separated and the aqueous phase was extracted DCM (2×25 mL). The organic phases were combined, dried over sodium sulfate, filtered, and concentrated. The crude residue obtained was purified by silica gel column chromatography using a gradient 50-100% ethyl acetate in hexanes to give 6-amino-3-hydroxy-3-(trifluoromethyl)indolin-2-one (921 mg, 99%)

1. filtrationThe catalyst was filtered off through Celite
2. concentrationthe filtrate was concentrated to dryness
3. customThe crude residue obtained
4. customwas partitioned between DCM (25 mL) and aqueous saturated NaHCO3 (15 mL)
5. customThe organic phase was separated
6. extractionthe aqueous phase was extracted DCM (2×25 mL)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude residue obtained
11. customwas purified by silica gel column chromatography

ORD record

ord-bedb7249ed8246e29228621ee9407571

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748612B2