5-(2-Methoxy-4-nitrophenyl)oxazole → 3-Methoxy-4-(oxazol-5-yl)aniline

In a 2 L hydrogenation flask was placed 1C (130.0 g, 0.6131 mol), Pd/C (10%, 26.2 g) and absolute EtOH (1280 mL). The mixture was hydrogenated at 35–45 psi H2 until the reaction was complete. The mixture was filtered over a pad of celite (20 g) and the cake was washed with EtOH (3×100 mL). The filtrate was concentrated to a volume of 350 mL. Heptane (500 mL) was added to the resulting slurry. After stirring for 2 hours at room temperature, the slurry was filtered. The cake was washed with heptane (3×100 mL) and air-dried to give 80.0 g of 1D. Another 30.2 g of product was recovered from the mother liquor affording a total yield of 95%. 1H NMR (CDCl3) d 7.88 (s, 1H), 7.60 (d, J=8.4 Hz, 1H), 7.41 (s, 1H), 6.41 (dd, J=8.4, 2.1 Hz, 1H), 3.34 (d, J=2.1 Hz, 1H), 3.98 (bs, 2H), 3.94 (s, 3H).

1. customIn a 2 L hydrogenation flask was placed
2. filtrationThe mixture was filtered over a pad of celite (20 g)
3. washthe cake was washed with EtOH (3×100 mL)
4. concentrationThe filtrate was concentrated to a volume of 350 mL
5. additionHeptane (500 mL) was added to the resulting slurry
6. filtrationthe slurry was filtered
7. washThe cake was washed with heptane (3×100 mL)
8. customair-dried

ORD record

ord-8ec89a30cdb544d79522f4c87e16614c

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07060720B2