Water → 8-Chloro-1-oxo-1,2,3,4-tetrahydroisoquinolin-7-yl diethylcarbamate

HRID 577475Notes

Reaction equation

[Cl:1][C:2]1[C:3]([OH:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[NH:9][CH2:8][CH2:7]2.[CH2:14]([N:16]([CH2:20][CH3:21])[C:17](Cl)=[O:18])[CH3:15].O>N1C=CC=CC=1>[CH2:14]([N:16]([CH2:20][CH3:21])[C:17](=[O:18])[O:13][C:3]1[C:2]([Cl:1])=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][C:10]2=[O:12])=[CH:5][CH:4]=1)[CH3:15]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 8-chloro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one (1e, 5.6 g, 28 mmol), and diethylcarbamic chloride (4.3 g, 31 mmol) in pyridine (100 mL) was stirred at 100° C. for 5 hours. To the reaction mixture was added H2O (300 mL). The mixture was extracted with EtOAc (2×200 mL). The combined organic layers were washed with 1 N HCl (2×300 mL) and brine (300 mL), dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography (EtOAc) to give 8-chloro-1-oxo-1,2,3,4-tetrahydroisoquinolin-7-yl diethylcarbamate (1f, 7.6 g, 90%) as brown oil.

Workup

extractionThe mixture was extracted with EtOAc (2×200 mL)
washThe combined organic layers were washed with 1 N HCl (2×300 mL) and brine (300 mL)
dry with materialdried over Na2SO4
concentrationconcentrated under vacuum
customThe residue was purified by column chromatography (EtOAc)

Sources & evidence

ORD record: ord-969d990123b94241bb506c542386a2f9
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040515B2

Reaction notes

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