Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:14][N:15]3C(=O)C4C(=CC=CC=4)C3=O)[O:13][CH2:12][CH2:11][O:10]2)=[CH:5][CH:4]=1.O.NN.[OH-].[Na+].O>C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([CH2:14][NH2:15])[O:10][CH2:11][CH2:12][O:13]2)=[CH:7][CH:8]=1Participants
Procedure
2-[2-(4-Methoxyphenyl)-[1,3]dioxolan-2-ylmethyl]isoindole-1,3-dione (Preparation 41, 2.0 g, 5.90 mmol) and hydrazine hydrate (5 mL) were combined. The stirred reaction mixture was heated under reflux for 48 h then allowed to cool to rt. Aqueous sodium hydroxide (2M, 10-15 mL) and water (20 mL) were added and the mixture stirred until a solution was formed. Diethyl ether (20 mL) was added and the biphasic mixture stirred vigorously for 16 h. The layers were separated and the aqueous layer was extracted with diethyl ether (3×20 mL), then the combined organic extracts were washed with brine (20 mL). The ethereal solution was passed through a filter paper then evaporated to dryness in vacuo to give the title compound as a yellow oil, which solidified on standing. δH (CDCl3): 1.42 (2H, br s), 3.06 (2H, s), 3.97 (3H, s), 4.00 (2H, t), 4.21 (2H, t), 7.04 (2H, d), 7.53 (2H, d).
Workup
- customThe stirred reaction mixture
- temperaturewas heated
- temperatureunder reflux for 48 h
- customwas formed
- stirringthe biphasic mixture stirred vigorously for 16 h
- customThe layers were separated
- extractionthe aqueous layer was extracted with diethyl ether (3×20 mL)
- washthe combined organic extracts were washed with brine (20 mL)
- customthen evaporated to dryness in vacuo
Sources & evidence
- ORD record
- ord-8db2feb54cfa4940aafe6d5972ae9859
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158622B2
Linked notes
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