Methanol → 2-Methyl-4-propoxyaniline

Compound 404b (3.78 g, 19.4 mmol) was dissolved in EtOAc (20 mL) and MeOH (20 mL) and transferred to a 250 mL hydrogenation flask. 10% Pd/C (378 mg, 10% w/w) was added and the sample was hydrogenated for 4 h at 35 psi H2. Upon completion, the mixture was filtered over a bed of Celite and then concentrated in vacuo. The residue was dissolved in EtOAc (100 mL) and washed with NaHCO3 (100 mL×3). The organic layer was separated and then dried over Na2SO4 to provide a crude brown oil which was further purified by chromatography (20% to 50% EtOAc/hexanes) to yield an amber oil (2.72 g, 85%): TLC Rf 0.27 (20% EtOAc/hexanes). 1NMR (600 MHz, CDCl3) δ 6.67 (s, 1H), 6.62 (m, 2H), 3.85-3.38 (t, 2H, J=6.66 Hz), 2.16 (s, 3H), 1.79-1.73 (sex, 2H, J=7.44 Hz), 1.02-1.00 (t, 3H, J=7.44 Hz). 13C NMR (150 MHz, CDCl3) δ 152.3, 137.8, 124.1, 117.2, 116.1, 112.9, 70.1, 22.7, 17.7, 10.5. Elemental analysis calculated for C10H15NO: C, 72.69; H, 9.15; N, 8.48. Found: C, 72.42; H, 9.14; N, 8.46.

1. filtrationUpon completion, the mixture was filtered over a bed of Celite
2. concentrationconcentrated in vacuo
3. dissolutionThe residue was dissolved in EtOAc (100 mL)
4. washwashed with NaHCO3 (100 mL×3)
5. customThe organic layer was separated
6. dry with materialdried over Na2SO4
7. customto provide a crude brown oil which
8. customwas further purified by chromatography (20% to 50% EtOAc/hexanes)

ORD record

ord-72aba9b8cf73493aaa6a4378c9cc9b93

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09061994B1