Reaction equation
[C:1]([CH2:3][N:4]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]1[C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:2].[ClH:15].[CH2:16]([O:18]CC)[CH3:17].C(O)C>>[ClH:15].[CH2:16]([O:18][C:1](=[NH:2])[CH2:3][N:4]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:17]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
A high pressure reaction vessel charged with ethyl 1-(cyanomethyl)-5-methyl-1H-pyrrole-2-carboxylate (848 mg, 4.41 mmol) cooled to 0° C. was treated with a 2M solution of hydrochloric acid in diethyl ether (30 mL, 60 mmol) and absolute ethanol (406 mg, 8.82 mmol). The mixture was stirred at 0° C. for 10 min and then was warmed to room temperature where it stirred over the weekend. At this time, the mixture was diluted with hexanes. The resulting precipitate was collected by filtration to afford ethyl 1-(2-ethoxy-2-iminoethyl)-5-methyl-1H-pyrrole-2-carboxylate hydrochloride (1.16 g, 95.7%) as a white solid. LC-MS calcd. for C12H19N2O3 [(M+H)+] 239, obsd. 239.0.
Workup
- customA high pressure reaction vessel
- temperaturewas warmed to room temperature where it
- stirringstirred over the weekend
- filtrationThe resulting precipitate was collected by filtration
Sources & evidence
- ORD record
- ord-74d36ae72802488f9990d44583f7963c
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841299B2
Linked notes
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