Methylamine → HCID 60905559, compound

A solution of methylamine (64 mL of a 2.0 M solution in MeOH, 128 mmol) was added to 2-isobutoxy-3-methoxybenzaldehyde (2.45 g, 11.9 mmol) and the solution was stirred for 18 h. The solution was concentrated under reduced pressure. The resulting clear oil was dissolved in EtOH (64 mL) and treated with NaBH4 (0.616 g, 16.3 mmol). After stirring for 7 h, the mixture was concentrated under reduced pressure and then dissolved in 1 N NaOH (57 mL). The mixture was extracted with Et2O (3×75 mL). The combined organics were washed with brine (2×100 mL), dried (Na2SO4) and concentrated to yield the title compound (2.43 g, 91%) as a light yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.01-6.88 (m, 3H), 3.76 (s, 3H), 3.63 (t, J=6.4 Hz, 3H), 2.25 (s, 3H), 2.00-1.93 (m, 1H), 1.84 (br s, 1H), 0.98 (d, J=6.6 Hz, 6H).

1. concentrationThe solution was concentrated under reduced pressure
2. dissolutionThe resulting clear oil was dissolved in EtOH (64 mL)
3. stirringAfter stirring for 7 h
4. concentrationthe mixture was concentrated under reduced pressure
5. dissolutiondissolved in 1 N NaOH (57 mL)
6. extractionThe mixture was extracted with Et2O (3×75 mL)
7. washThe combined organics were washed with brine (2×100 mL)
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated

ORD record

ord-3e34b6e4c0c6444389428b525a8e4c26

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450307B2