Methylamine → HCID 59277580, compound

A solution of methylamine (19 mL of a 2.0 M solution in MeOH, 38 mmol) was added to 2-propoxy-3-trifluoromethoxybenzaldehyde (1.15 g, 4.60 mmol). The mixture was stirred for 18 h. The solution was concentrated under reduced pressure. The resulting clear oil was dissolved in EtOH (19 mL) and treated with NaBH4 (0.174 g, 4.60 mmol). After stirring for 5.5 h, the reaction mixture was concentrated under reduced pressure, then dissolved in 1 N NaOH (19 mL). The mixture was extracted with Et2O (3×50 mL). The organics were collected, washed with brine (2×100 mL), dried (Na2SO4) and concentrated to yield the title compound (0.89 g, 73%) as an orange oil: 1H NMR (300 MHz, DMSO-d6) δ 7.41 (dd, J=7.7, 1.6 Hz, 1H), 7.25 (dd, J=6.7, 1.3 Hz, 1H), 7.16 (t, J=7.7 Hz, 1H), 3.87 (t, J=6.3 Hz, 2H), 3.68 (s, 2H), 2.27 (s, 3H), 2.07 (br s, 1H), 1.74 (q, J=6.4 Hz, 2H), 1.02 (t, J=3.1 Hz, 3H).

1. concentrationThe solution was concentrated under reduced pressure
2. dissolutionThe resulting clear oil was dissolved in EtOH (19 mL)
3. stirringAfter stirring for 5.5 h
4. concentrationthe reaction mixture was concentrated under reduced pressure
5. dissolutiondissolved in 1 N NaOH (19 mL)
6. extractionThe mixture was extracted with Et2O (3×50 mL)
7. customThe organics were collected
8. washwashed with brine (2×100 mL)
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated

ORD record

ord-de8541b1049e41cca41c68279a0e17f5

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450307B2