Hydrochloric Acid → HCID 71512857, compound

Temperature

0 °C

To 5-methoxy-2-methyl-4-nitroaniline (4.9 g, 26.8 mmol) in a mixture of acetone (17.5 mL) and water (19 mL) at 0° C. was added conc. HCl (5.6 mL). A solution of sodium nitrite (2.25 g, 32.6 mmol) in water (7.5 mL) was added dropwise and the mixture was allowed to stir at 0° C. for 30 min. The mixture was then added dropwise to a mixture of copper cyanide (3.75 g, 42 mmol) and sodium cyanide (5.5 g, 112 mmol) in water (25 mL) and EtOAc (12.5 mL). The mixture was allowed to stir at RT for 2 h and then water (50 mL) was added. The mixture was extracted with EtOAc (3×100 mL) and the combined organic fractions were washed with 2 M NaOH(aq) (50 mL) and brine (50 mL). The organic fraction was passed through a hydrophobic frit and the solvent was removed in vacuo. The residue was triturated with iso-hexane and dried to give 5-methoxy-2-methyl-4-nitrobenzonitrile (4.62 g, 90%) as an off-white solid. LCMS (10 cm_ESCI_Bicarb_MeCN): [M]−=192 at 3.19 min. 1H NMR (400 MHz, CDCl3): δ 7.72 (s, 1H), 7.31 (s, 1H), 3.98 (s, 3H), 2.55 (s, 3H).

1. stirringto stir at RT for 2 h
2. extractionThe mixture was extracted with EtOAc (3×100 mL)
3. washthe combined organic fractions were washed with 2 M NaOH(aq) (50 mL) and brine (50 mL)
4. customthe solvent was removed in vacuo
5. customThe residue was triturated with iso-hexane
6. customdried

ORD record

ord-f09a98f7a24f4812b808c6342c6709a2

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809331B2