Ethylene Glycol → HCID 14008100, compound

HRID 1892023Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:23])[N:7]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[C:8](=[O:15])[C:9]3[C:14]=2[C:13]=1[CH:12]=[CH:11][CH:10]=3.[OH-].[Na+].[CH2:26]([OH:29])[CH2:27][OH:28]>O>[OH:28][CH2:27][CH2:26][O:29][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:23])[N:7]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[C:8](=[O:15])[C:9]3[C:14]=2[C:13]=1[CH:12]=[CH:11][CH:10]=3

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 6-bromo-2-p-tolyl-benzo[de]isoquinoline-1,3-dione (4.0 g), sodium hydroxide (0.65 g), and 1,2-ethylene glycol (50 ml) was maintained under reflux with stirring at 120° C. for 10 hrs. The reaction mixture was then cooled to room temperature and water (100 ml) was added to the mixture. The solid that separated out was filtered, washed with water, and dried at 100° C. for 8 hours (Yield=2.71 g). The crude product was purified using 120 ml monochlorobenzene and 0.25 g activated charcoal to obtain pure product weighing 1.32 g. H1-NMR: 2.39 δ (s, 3 protons); 3.92 δ (m, 2 proton); 4.35 δ (t, 2 protons); 5.13 δ (t, 1 proton); 7.22 δ (m, 2 protons); 7.31 δ (m, 3 protons); 7.83 δ (t, 1 proton); 8.44δ (m, 2 protons); 8.68 δ (d, 1 proton).

Workup

temperaturewas maintained
temperatureunder reflux
temperatureThe reaction mixture was then cooled to room temperature
customThe solid that separated out
filtrationwas filtered
washwashed with water
customdried at 100° C. for 8 hours (Yield=2.71 g)
customThe crude product was purified
customto obtain pure product

Sources & evidence

ORD record: ord-74f0193fa4d346b788d95c5125456f1b
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507590B2

Reaction notes

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