Water → 1-(7-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one
Reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20].O>ClCCl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:19](=[O:21])[CH3:20])[CH2:9]2)=[CH:4][CH:3]=1Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To A mixture of 7-bromo-1,2,3,4-tetrahydroisoquinoline (500 mg, 2.36 mmol) and triethylamine (715 mg, 7.08 mmol) in dichloromethane (10 mL) was added acetyl chloride (221 mg, 2.83 mmol) at 0° C., then the mixture was stirred for 2 h at 0° C. Water (5 mL) was added and the mixture extracted with ethyl acetate (10 mL). The combined organic layers were washed with brine (3×10 mL) and dried with Na2SO4. The residue was concentrated then purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=5:1) to give 1-(7-bromo-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (500 mg, 83%) as yellow oil. LC-MS: [M+H]+, 254, tR=1.533 min.
Workup
- extractionthe mixture extracted with ethyl acetate (10 mL)
- washThe combined organic layers were washed with brine (3×10 mL)
- dry with materialdried with Na2SO4
- concentrationThe residue was concentrated
- customthen purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=5:1)
Sources & evidence
- ORD record
- ord-317668d6de104d738a25364f7e09931d
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09169259B2
Reaction notes
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