Methylamine → HCID 66967533, compound

A solution of methylamine (20 mL of a 2.0 M solution if MeOH, 40 mmol) was added to 2-ethoxy-3-trifluoromethoxybenzaldehyde (1.17 g, 4.95 mmol) under N2 and the solution was stirred for 18 h. The solution was concentrated under reduced pressure. The resulting clear oil was dissolved in EtOH (20 mL) and treated with NaBH4 (0.187 g, 4.95 mmol). After stirring for 5.5 h, the reaction mixture was concentrated under reduced pressure, then dissolved in 1 N NaOH (20 mL) and extracted with Et2O (3×50 mL). The combined organics were collected, washed with brine (2×100 mL), dried (Na2SO4) and concentrated to yield the title compound (0.72 g, 58%) as a clear oil: 1H NMR (500 MHz, DMSO-d6) δ 7.40 (dd, J=7.7, 1.55 Hz, 1H), 7.25 (d, J=9.5 Hz, 1H), 7.16 (t, J=7.7 Hz, 1H), 3.97 (t, J=7.0 Hz, 2H), 3.68 (s, 2H), 2.28 (s, 3H), 2.02 (br s, 1H), 1.35-1.30 (m, 3H).

1. concentrationThe solution was concentrated under reduced pressure
2. dissolutionThe resulting clear oil was dissolved in EtOH (20 mL)
3. stirringAfter stirring for 5.5 h
4. concentrationthe reaction mixture was concentrated under reduced pressure
5. dissolutiondissolved in 1 N NaOH (20 mL)
6. extractionextracted with Et2O (3×50 mL)
7. customThe combined organics were collected
8. washwashed with brine (2×100 mL)
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated

ORD record

ord-3ea1832c9137445aba44c796f6ed99bd

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450307B2