Ammonium Chloride → HCID 86615261, compound

HRID 1932377Notes

Reaction equation

HRID 1932377 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9]2)[C:5]([N+:18]([O-])=O)=[CH:4][CH:3]=1.[CH3:21][C:22]([Mg]Br)=[CH:23][CH3:24].[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:23]([CH3:24])=[C:22]([CH3:21])[NH:18][C:5]2=[C:6]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9]2)[N:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 431526772-(6-Chloro-3-nitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinolineHCID 178448414HCID 178448414, compound

Product 1

HCID 86615261HCID 86615261, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

2-(6-Chloro-3-nitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline (16 g, 56.6 mmol) prepared in Preparation 7 was dissolved in anhydrous tetrahydrofuran (300 ml) under a nitrogen atmosphere. 1-Methyl-1-propenyl magnesium bromide (0.5M in tetrahydrofuran solution, 283 ml, 141.5 mmol) was slowly added at −78° C. to the solution. The reaction mixture was stirred for 2 hours at −20° C. and then 20% (w/v) ammonium chloride solution was added thereto. The reaction mixture was extracted with ethyl acetate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/10, v/v) to give 7.8 g of the titled compound as yellow oil. (Yield: 45%)

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/10

Sources & evidence

ORD record
ord-f1914a9d225a49aaba7a6e74004e65db
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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