Acetic Acid → HCID 58009327, compound

Temperature

140 °C

Under an atmosphere of nitrogen was added to a solution of 4-chloro-2-methylbenzaldehyde (10.0 g, 64.9 g) in acetic acid (70 mL) ammonium acetate (11.5 g, 149 mmol) and nitromethane (10.0 ml, 185 mmol). The solution was stirred at reflux (oil bath 140° C.) for 2 h. After cooling to ambient temperature water (70 mL) was added and extracted twice with ethyl acetate (70 mL). The organic layers were washed with water (70 mL) and brine (70 mL) and were dried over sodium sulfate. The filtrated was concentrated and the resulting solid was suspended in methanol (30 mL), at 0° C. filtered off and was washed with cold methanol (10 mL) affording the title compound (8.30 g, 65%) as a yellow solid. MS m/e: 197.0 [M]+.

1. additionwas added
2. extractionextracted twice with ethyl acetate (70 mL)
3. washThe organic layers were washed with water (70 mL) and brine (70 mL)
4. dry with materialwere dried over sodium sulfate
5. concentrationThe filtrated was concentrated
6. customwas suspended in methanol (30 mL), at 0° C.
7. filtrationfiltered off
8. washwas washed with cold methanol (10 mL)

ORD record

ord-7e1275bd9f4c45bea31d2edfee43eb6e

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08404679B2