Reaction equation
[CH3:1][C:2]1[O:3]CC[N:6]=1.[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[OH:17].[C:18](OCC)(=O)[CH3:19]>>[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[O:17][CH2:18][CH2:19][CH2:1][C:2]([NH2:6])=[O:3]Participants
Conditions
- Temperature
- 70 °C
Procedure
A 3-neck round bottom flask was charged with 2-methyl-2-oxazoline (5.9 mL, 69.4 mmol) followed by 2-naphthol (10.0 g, 69.4 mmol) at room temperature. The resulting mixture was heated to reflux and stirred for 6 h. Reaction was monitored by TLC analysis. Additional 2-methyl-2-oxazoline (2.5 mL, 29.4 mmol) was added to ensure complete conversion of the 2-naphthol and the reaction mixture was heated to reflux for 16 additional hours. The reaction mixture was cooled to 70° C. then poured into ethyl acetate (100 mL) and stirred for 15 min. The resulting slurry was filtered and washed with ethyl acetate (25 mL). The filter cake was further dried under vacuum to afford -(2-(naphthalen-2-yloxy)ethyl)acetamide as an off white solid (12.35 g, 77.7% yield). 1H NMR (DMSO-d6, 400 MHz) δ 8.179-8.126 (m, 1H), 8.84-7.79 (m, 3H), 7.7.48-7.43 (m, 1H), 7.37-7.32 (m, 2H), 7.18 (dd, j=2.59 Hz, 8.97 Hz, 1H) 4.11 (t, j=5.66, 2H), 3.48 (q, j=5.90 Hz, 2H), 1.85 (s, 3H).
Workup
- temperatureThe resulting mixture was heated
- temperatureto reflux
- customReaction
- temperaturethe reaction mixture was heated
- temperatureto reflux for 16 additional hours
- stirringstirred for 15 min
- filtrationThe resulting slurry was filtered
- washwashed with ethyl acetate (25 mL)
- customThe filter cake was further dried under vacuum
Sources & evidence
- ORD record
- ord-bf38e48ca1c144df9fb40148915f6792
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115237B2
Linked notes
Loading…