Ammonium Chloride → HCID 57532252, compound

Temperature

85 °C

Iron powder (6.1 g, 109 mmol) was added to a suspension of (4-bromo-3-methyl-5-nitro-phenyl)-carbamic acid 2-trimethylsilanyl-ethyl ester (Example 294: step c (4.1 g, 10.9 mmol)) and NH4Cl (5.84 g, 109 mmol) in EtOH (27 mL) and water (54 mL). The reaction was heated at 85° C. for 14 h. The cooled mixture was filtered through celite and the solids were washed with 1:1 EtOAc/MeOH (200 mL). The filtrate was concentrated in vacuo and the residue was partitioned between EtOAc (100 mL) and H2O (30 mL). The organic solution was washed with water (30 mL), and brine (50 mL). Drying and concentration of the solution yielded the title compound (3.24 g, 86%) as a brown solid which was used without further purification. 1H NMR (CDCl3) δ 6.96 (s, 1H), 6.54 (s, 1H), 6.39 (s, 1H), 4.26 (m, 2H), 4.16 (s, 2H), 2.35 (s, 3H), 1.06 (m, 2H), 0.08 (s, 9H).

1. filtrationThe cooled mixture was filtered through celite
2. washthe solids were washed with 1:1 EtOAc/MeOH (200 mL)
3. concentrationThe filtrate was concentrated in vacuo
4. customthe residue was partitioned between EtOAc (100 mL) and H2O (30 mL)
5. washThe organic solution was washed with water (30 mL), and brine (50 mL)
6. customDrying

ORD record

ord-b8e49f8919204b6b826a2d780d45eab5

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07138530B2