Sodium ethoxide → 4-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)aniline

HRID 48250Notes

Reaction equation

HRID 48250 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([NH:20]C(=O)C)=[CH:16][CH:15]=1.C([O-])C.[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 2723922Sodium ethoxide2×HCID 9902940N-(4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl)acetamide2×

Product 1

HCID 99443944-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)aniline

Procedure

3.0 g (8.59 mmol) of N-[4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)-phenyl]acetamide (example 3, intermediate 5) were heated to reflux in 100 ml of 21% strength sodium ethanolate solution. Solid sodium ethanolate was added depending on the progress of the reaction, until complete conversion was achieved. For workup, the solvent was removed and the residue was taken up in H2O. It was extracted twice with dichloromethane. The combined organic phases were dried with MgSO4 and concentrated. Further purification takes place by chromatography on silica gel with an ethyl acetate/heptane mixture, resulting in the aniline compound as a yellow oil.

Workup

  1. customdepending on the progress of the reaction, until complete conversion
  2. customFor workup, the solvent was removed
  3. extractionIt was extracted twice with dichloromethane
  4. dry with materialThe combined organic phases were dried with MgSO4
  5. concentrationconcentrated
  6. customFurther purification

Sources & evidence

ORD record
ord-7fc4fcd197144a75bef167c6e00014f3
Source dataset
uspto-grants-2004_03
Patent number
US06703405B2

Reaction notes

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