Ammonium Chloride → 7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochloride
Reaction equation
[CH3:1][C:2]([Mg]Br)=[CH:3][CH3:4].[CH2:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][N:8]1[C:17]1[C:22]([N+:23]([O-])=O)=[CH:21][CH:20]=[CH:19][N:18]=1.[Cl-:26].[NH4+]>O1CCCC1>[ClH:26].[CH2:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][N:8]1[C:17]1[N:18]=[CH:19][CH:20]=[C:21]2[C:3]([CH3:4])=[C:2]([CH3:1])[NH:23][C:22]=12Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
1-Methyl-1-propenyl magnesium bromide (0.5M in tetrahydrofuran solution; 112 ml) was slowly added at −78° C. to a solution of 2-(1,2,3,4-tetrahydroisoquinolin-2-yl)-3-nitropyridine (4.8 g, 18.8 mmol) prepared in Preparation 20 in anhydrous tetrahydrofuran (150 ml). The reaction mixture was stirred for 4 hours at −20° C. 20% ammonium chloride solution was added to the reaction mixture, which was then extracted with ethyl acetate. The separated organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1, v/v). The resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give 1.3 g of the titled compound as yellow solid.
Workup
- extractionwas then extracted with ethyl acetate
- dry with materialThe separated organic layer was dried on anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1
- dissolutionThe resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas
- filtrationfiltered
Sources & evidence
- ORD record
- ord-e9ad34702a4f42b0a2f5fa2570519dea
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188114B2
Reaction notes
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