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CAS No. : | 327183-29-9 | MDL No. : | |
Formula : | C14H21NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 267.33 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Stage #1: With hydrogen bromide In water; acetic acid at 20℃; for 4 h; Heating / reflux Stage #2: With sodium hydroxide In water; acetic acid |
2-(2'-Hydroxyethyl)-3-methoxy-N-tert-butoxycarbonyl-aniline (158 g, 0.59 mol) was added portionwise to a stirred solution of hydrogen bromide in acetic acid (30percent, 1.7 L) at room temperature. The reaction was then heated to reflux for 4 h. The reaction mixture was cooled to room temperature, basified to pH 14 with aqueous sodium hydroxide solution (6 N) and extracted with dichloromethane (3*2 L). The organic extracts were combined, dried (magnesium sulphate) and evaporated to give the title compound as an orange oil (78 g, 92percent); NMR (400 MHz, CDCl3) δH 2.99 (2H, t, J 8.5 Hz), 3.55 (2H, br s), 4.57 (2H, t, J 8.5 Hz), 6.19 (1H, d, J 7.5 Hz), 6.25 (2H, d, J 7.5 Hz), 6.92 (1H, t, J 8.0 Hz); IR νmax (Nujol)/cm-1 2853, 2610, 1544, 1462, 1262, 1234, 986 and 761. |