Hydrochloric Acid → HCID 60134441, compound

To a stirred solution of 2-nitropropane (20.0 g, 0.22 mol), 2-(methylamino)ethanol (19.7 mL, 1.1 equiv, 0.24 mol) and 5 N NaOH (0.24 mL, 0.005 equiv, 1.2 mmol) in a mixture of isopropanol (34 mL) and water (3.4 mL) was added dropwise a 37% solution of formaldehyde (18.2 mL, 1.1 equiv, 0.24 mol) over 15 min. The reaction was left to stir for 17 h then the solvent was removed in vacuo. 4 M HCl in dioxanes (66 mL, 0.26 mol) was added to the residue and the solvent removed in vacuo to give an oily residue. The oil was triturated with a mixture of isopropanol and anhydrous diethyl ether to give a hygroscopic white powder. The white powder was dissolved into water (100 mL) and 5 N NaOH (35 mL) was added to give a pale yellow green oil. The oil was extracted with DCM (150 mL) and the organic layer washed with water (2×100 mL), dried over anhydrous MgSO4, filtered and concentrated to a pale yellow green oil (28.0 g, 71.6%). 1H NMR (CDCl3, 400 MHz): δ 1.59 (s, 6H), 2.30 (s, 3H), 2.35-2.38 (t, J=11.2, 1H), 2.63-2.65 (t, J=5.6, 2H), 2.93 (s, 2H), 3.53-3.57 (q, J=5.3, 2H). LRMS (ESI+) for C7H16N2O3 (176.1); Found: 177 (MH+).

1. waitThe reaction was left
2. customthe solvent was removed in vacuo
3. customthe solvent removed in vacuo
4. customto give an oily residue
5. customThe oil was triturated with a mixture of isopropanol and anhydrous diethyl ether
6. customto give a hygroscopic white powder
7. additionwas added
8. customto give a pale yellow green oil
9. extractionThe oil was extracted with DCM (150 mL)
10. washthe organic layer washed with water (2×100 mL)
11. dry with materialdried over anhydrous MgSO4
12. filtrationfiltered
13. concentrationconcentrated to a pale yellow green oil (28.0 g, 71.6%)

ORD record

ord-02ac794de86b47f1910b4b95cf5a5cc0

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278482B2