Ammonium Chloride → HCID 68705712, compound

HRID 1988832Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1)([O-])=O.[CH3:20][C:21]([Mg]Br)=[CH:22][CH3:23].[Cl-].[NH4+]>O1CCCC1>[CH3:20][C:21]1[NH:1][C:4]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)[C:22]=1[CH3:23]

Participants

Conditions

Temperature: -20 °C

Procedure

2-(3-Nitropyridin-4-yl)-1,2,3,4-tetrahydroisoquinoline (5 g, 19.58 mmol) prepared in Preparation 1 was dissolved in anhydrous tetrahydrofuran (200 ml) under a nitrogen atmosphere. 1-Methyl-1-propenyl magnesium bromide (0.5M in tetrahydrofuran solution, 80 ml, 117.5 mmol) was added at −78° C. to the solution, which was then stirred for 5 hours at −20° C. 20 ml of 20% ammonium chloride solution was added to the reaction mixture, which was then extracted with ethyl acetate (200 ml) twice. 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/methylene chloride/methanol=10/10/1, (v/v/v)) to give the titled compound as a pale yellow solid (2.1 g, 25.3%).

Workup

extractionwas then extracted with ethyl acetate (200 ml) twice
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/methylene chloride/methanol=10/10/1, (v/v/v))

Sources & evidence

ORD record: ord-5860c3d775c546dcb6f7f7903154858a
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642269B2

Reaction notes

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