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
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>[O-]CC.[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]=1Participants
3
Procedure
3.0 g (8.6 mmol) of N-[4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]acetamide (intermediate 5) were dissolved in 100 ml of 20% sodium ethoxide solution and heated to reflux for 4 hours. A further 2.0 g (29.4 mmol) of solid sodium ethoxide were added and the mixture was heated to reflux for another 3 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. For further purification, chromatography was effected on silica gel (1:1 ethyl acetate/heptane) to obtain the aniline as a yellowish oil in quantitative yield.
Workup
- temperatureheated
- temperatureto reflux for 4 hours
- temperaturethe mixture was heated
- temperatureto reflux for another 3 hours
- customFor workup, the solvent was removed in vacuo
- extractionextracted twice with dichloromethane
- dry with materialThe combined organic phases were dried with MgSO4
- concentrationconcentrated
- customFor further purification, chromatography
Sources & evidence
- ORD record
- ord-811e96aba13c4d8f813cf3f66f66528d
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07241775B2
Reaction notes
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