Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitric Acid | HCID 944 | — |
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | 2-(Methylamino)ethanol | HCID 8016 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 21075976 | HCID 21075976 | 82% |
Reaction Steps
Methyl(2-(hydroxy)ethyl)amine (1.5 g, 20 mmol) in EtOAc (65 mL) was added drop-wise to a mixture of fuming HNO3 (6.3 g, 4.2 mL, 100 mmol) and Ac2O (16.3 g, 15.1 mL, 160 mmol) at −10° C. The reaction mixture was stirred at −10° C. for 30 minutes and diluted with EtOAc and hexane. The precipitate was collected by filtration and washed with hexane to give the title compound (2.79 g, 82% yield) as an off-white solid. Mp 58-62° C. 1H NMR (300 MHz, d6-DMSO) δ 4.59-4.67 (m, 2H), 4.64-4.73 (m, 2H), 2.61 (bs, 3H). 13C NMR (75 MHz, d6-DMSO) δ 59.8, 38.7, 24.4. Mass spectrum (API-TIS) m/z 121 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07754772B2 |
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| Source dataset | uspto-grants-2010_07 |
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| ORD ID | ord-baa86a52592a4a7985bde7b2fda39072 |
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| Source note | uspto-grants-2010_07 |
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