Acetic Acid → 4-Chloro-2-(4-methoxybenzyl)-1-oxo-1,2-dihydroisoquinoline-7-sulfonyl chloride

HRID 1473699Notes

Reaction equation

C(S[C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:29])=[CH:14][N:15]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[C:16]2=[O:19])=[CH:11][CH:10]=1)C1C=CC=CC=1.C(Cl)Cl.C(O)(=O)C.[S:37]([Cl:41])(Cl)(=[O:39])=[O:38]>O>[Cl:29][C:13]1[C:12]2[C:17](=[CH:18][C:9]([S:37]([Cl:41])(=[O:39])=[O:38])=[CH:10][CH:11]=2)[C:16](=[O:19])[N:15]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A round bottomed flask cooled to 0° C., was charged 7-(benzylthio)-4-chloro-2-(4-methoxybenzyl)isoquinolin-1(2H)-one (0.400 g, 0.948 mmol), DCM (9.03 ml), Acetic Acid (0.226 ml), and Water (0.226 ml). After stirring for 5 minutes at 0° C., sulfuryl chloride (0.077 ml, 0.948 mmol) was added and stirring was continued for an additional 1 hour at 0° C. The reaction was concentrated, dissolved in minimal DCM and purified via column chromatography (silica gel 40 g, gradient elution 0 to 50% EtOAc:Heptane) to afford 0.342 g of 4-chloro-2-(4-methoxybenzyl)-1-oxo-1,2-dihydroisoquinoline-7-sulfonyl chloride. m/z (ESI) 399.2 (M+H)+.

Workup

stirringstirring
waitwas continued for an additional 1 hour at 0° C
concentrationThe reaction was concentrated
dissolutiondissolved in minimal DCM
custompurified via column chromatography (silica gel 40 g, gradient elution 0 to 50% EtOAc:Heptane)

Sources & evidence

ORD record: ord-0eeac962064c49fe8b4a9ec62378e696
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012443B2

Reaction notes

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