Ethylenediamine → 1-(2-Imidazolin-2-YL)-7-methoxy-6-methyl-1,2,3,4-tetrahydronaphthalene

HRID 499014Notes

Reaction equation

HRID 499014 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH:10]2[C:13]#[N:14])=[CH:5][C:4]=1[CH3:15].[CH2:16](N)[CH2:17][NH2:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[NH:14]1[CH2:16][CH2:17][N:18]=[C:13]1[CH:10]1[C:11]2[C:6](=[CH:5][C:4]([CH3:15])=[C:3]([O:2][CH3:1])[CH:12]=2)[CH2:7][CH2:8][CH2:9]1

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 6101p-Toluenesulfonic acidHCID 675300557-Methoxy-6-methyl-1,2,3,4-tetrahydronaphthalenecarbonitrile

Product 1

HCID 675301181-(2-Imidazolin-2-YL)-7-methoxy-6-methyl-1,2,3,4-tetrahydronaphthaleneYield 57.3%

Procedure

This compound was prepared in a manner analogous to that of Step G of Example 1, by the reaction of 0.1 gram (0.0005 mole) of 7-methoxy-6-methyl-1,2,3,4-tetrahydronaphthalenecarbonitrile (iv) and 1.2 grams (0.0048 mole) of the ethylenediamine salt of p-toluenesulfonic acid (prepared in Step F of Example 1). The reaction product was purified by column chromatography on silica gel using mixtures of methylene chloride and methanol as an eluant. The appropriate fractions of eluate were combined and concentrated under reduced pressure, yielding 0.07 gram of subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that of Step G of Example 1
  2. customThe reaction product was purified by column chromatography on silica gel using mixtures of methylene chloride and methanol as an eluant
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-648d49d19f89454cb79725ae736bac68
Source dataset
uspto-grants-2010_08
Patent number
US07767667B2

Reaction notes

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