N-(4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl)acetamide → 4-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)aniline

HRID 1072512Notes

Reaction equation

HRID 1072512 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 1

HCID 9902940N-(4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl)acetamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent2×

Procedure

3.0 g (8.6 mmol) of N-[4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydro-isoquinolin-4-yl)-phenyl]-acetamide (example 1) was dissolved in 100 ml of 20% strength sodium ethanolate solution and heated under reflux for four hours. A further 2.0 g (29.4 mmol) of solid sodium ethanolate was added, and the mixture was heated under reflux for three more hours. For workup, the solvent was removed in vacuo, and the residue was taken up in 200 ml of H2O and extracted twice with dichloromethane. The combined organic phases were dried with MgSO4 and concentrated. Further purification by chromatography on silica gel (ethyl acetate/heptane 1:1) resulted in the aniline as a yellowish oil in quantitative yield.

Workup

  1. temperatureheated
  2. temperatureunder reflux for four hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for three more hours
  5. customFor workup, the solvent was removed in vacuo
  6. extractionextracted twice with dichloromethane
  7. dry with materialThe combined organic phases were dried with MgSO4
  8. concentrationconcentrated
  9. customFurther purification by chromatography on silica gel (ethyl acetate/heptane 1:1)

Sources & evidence

ORD record
ord-9808ca43f69c41f48142052917fab844
Source dataset
uspto-grants-2005_06
Patent number
US06911453B2

Reaction notes

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