Hydrochloric Acid → HCID 86680975, compound

HRID 333678Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([N+:22]([O-:24])=[O:23])=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[NH:9][C:10]2=[O:13])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][OH:34].Cl>CN(C=O)C>[OH:34][CH2:33][CH2:32][N:9]1[C:8]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[C:7]([N+:22]([O-:24])=[O:23])[C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:10]1=[O:13]

Participants

Conditions

Temperature: 50 °C

Procedure

In a 25-mL flask under argon, 7-methoxy-3-(4-methoxyphenyl)-4-nitroisoquinoline-1(2H)-one (compound D5, 150 mg, 0.46 mmol) is dissolved in 5 mL of DMF. Potassium carbonate (317 mg, 2.3 mmol) is then added. After stirring for 30 minutes, 2-bromoethanol (329 μl, 4.6 mmol) is added. Stirring is maintained for 24 hours at 50° C. Once returned to ambient temperature, the medium is neutralized with 20 mL of a 1N hydrochloric acid solution then extracted with 3×10 mL of ethyl acetate. The organic phases are washed with 3×10 ml of H2O, dried over MgSO4 and concentrated under vacuum. The residue obtained is chromatographed on a silica gel column using the cyclohexane-ethyl acetate mixture (60/40) as eluent in order to produce the expected 2-(2-hydroxyethyl)-7-methoxy-3-(4-methoxyphenyl)-4-nitroisoquinoline-1(2H)-one 68 (73 mg, 43%) in the form of a yellow solid.

Workup

stirringStirring
customOnce returned to ambient temperature
extractionthen extracted with 3×10 mL of ethyl acetate
washThe organic phases are washed with 3×10 ml of H2O
dry with materialdried over MgSO4
concentrationconcentrated under vacuum
customThe residue obtained
customis chromatographed on a silica gel column

Sources & evidence

ORD record: ord-3669aa5554cc4981a826f01b7a74fd34
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883763B2

Reaction notes

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