1-Bromo-3-chloropropane → 2-(3-Chloropropyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-one

HRID 2164050Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[C:11](=[O:17])[NH:10][CH2:9][CH2:8]2.Br[CH2:19][CH2:20][CH2:21][Cl:22]>CN(C)C=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[C:11](=[O:17])[N:10]([CH2:19][CH2:20][CH2:21][Cl:22])[CH2:9][CH2:8]2

Participants

Conditions

Temperature: 80 °C

Procedure

2.1 gm (44 millimols) of sodium hydride were added to a solution of 8.0 gm (41 millimols) of 6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one in 100 ml of dimethyl formamide, and the mixture was heated at 80° C. for 30 minutes. Then, 20 ml of 1-bromo-3-chloro-propane were added dropwise, and the mixture was heated at 100° C. for 3 hours. The solvent was then removed in vacuo, the solid residue was digested in water, and the aqueous mixture was extracted with chloroform several times. The combined organic extracts were dried over sodium sulfate and evaporated to dryness, and the evaporation residue was purified by chromatography on silica gel (chloroform/methanol = 150/l), yielding 3.2 gm of 1-(6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one-2-yl)-3-chloro-propane as a viscous oil having an Rf -value of 0.8 (ethyl acetate).

Workup

temperaturethe mixture was heated at 100° C. for 3 hours
customThe solvent was then removed in vacuo
extractionthe aqueous mixture was extracted with chloroform several times
dry with materialThe combined organic extracts were dried over sodium sulfate
customevaporated to dryness
customthe evaporation residue was purified by chromatography on silica gel (chloroform/methanol = 150/l)

Sources & evidence

ORD record: ord-06a546fcdf5e42e9b637fd15921f0dde
Source dataset: uspto-grants-1979_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04137318

Reaction notes

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