Ammonium Chloride → HCID 11594794, compound

HRID 1982901Notes

Reaction equation

HRID 1982901 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=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-:26].[NH4+]>O1CCCC1>[ClH:26].[CH3:20][C:21]1[NH:1][C:4]2[C:5]([N:10]3[CH2:19][CH2:18][C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH2:11]3)=[CH:6][N:7]=[CH:8][C:9]=2[C:22]=1[CH3:23]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 198160942-(4-Nitropyridin-3-yl)-1,2,3,4-tetrahydroisoquinolineHCID 178448414HCID 178448414, compound

Product 1

HCID 11594794HCID 11594794, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Nitropyridin-3-yl)-1,2,3,4-tetrahydroisoquinoline (2.0 g, 7.835 mmol) prepared in Preparation 2 was dissolved in anhydrous tetrahydrofuran (100 ml) under a nitrogen atmosphere. 1-Methyl-1-propenyl magnesium bromide (0.5M in tetrahydrofuran solution, 9.4 ml) was added at −78° C. to the solution, which was then stirred for 20 minutes at the same temperature. 10 ml of 20% ammonium chloride solution was added to the reaction mixture, which was then extracted with ethyl acetate (100 ml) twice. The separated organic layer was dried on anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (methylene chloride/methanol=10/1 (v/v)), dissolved in 5 ml of ethyl acetate and then saturated with hydrochloric acid gas. The resulting precipitate was filtered to give the titled compound as a white solid (850 mg, 19.5%).

Workup

  1. extractionwas then extracted with ethyl acetate (100 ml) twice
  2. dry with materialThe separated organic layer was dried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified with silica gel column chromatography (methylene chloride/methanol=10/1 (v/v))
  5. dissolutiondissolved in 5 ml of ethyl acetate
  6. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-ae74b642819d423ba1ee3c1d8eea41a3
Source dataset
uspto-grants-2009_06
Patent number
US07541366B2

Reaction notes

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