Chloride → HCID 49806216, compound

HRID 2381206Notes

Reaction equation

Cl[CH:2]1[NH+:11]2[CH2:12][CH2:13][C:14]3[C:19]([C:10]2=[C:9]([CH3:23])[C:8]2[CH:7]=[CH:6][C:5]([O:24][CH3:25])=[C:4]([O:26][CH3:27])[C:3]1=2)=[CH:18][C:17]1[O:20][CH2:21][O:22][C:16]=1[CH:15]=3.[Cl-].[CH2:29]([Mg]Br)[CH3:30].O1CC[CH2:35][CH2:34]1>C(OCC)C>[CH2:34]([C:2]1([CH2:29][CH3:30])[N:11]2[CH2:12][CH2:13][C:14]3[C:19]([C:10]2=[C:9]([CH3:23])[C:8]2[CH:7]=[CH:6][C:5]([O:24][CH3:25])=[C:4]([O:26][CH3:27])[C:3]1=2)=[CH:18][C:17]1[O:20][CH2:21][O:22][C:16]=1[CH:15]=3)[CH3:35]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 8-chloro-9,10-dimethoxy-13-methyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; chloride (1050 mg, 2.5 mmol) in anhydrous diethyl ether (50 mL) at 0° C. was added a solution of ethylmagnesium bromide in tetrahydrofuran (3 M, 9 mL, 27.4 mmol) dropwise. After stirring at 0° C. for 20 min, the reaction was quenched by adding saturated aqueous ammonium chloride solution (50 mL). The mixture was extracted with diethyl ether (2×100 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was re-crystallized from diethyl ether to afford 8,8-diethyl-9,10-dimethoxy-13-methyl-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (220 mg, 21%).

Workup

customthe reaction was quenched
additionby adding saturated aqueous ammonium chloride solution (50 mL)
extractionThe mixture was extracted with diethyl ether (2×100 mL)
washwashed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe residue was re-crystallized from diethyl ether

Sources & evidence

ORD record: ord-34a0fd4fbcd64fa4ab5a16e0c1410555
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258149B2

Reaction notes

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