Ethylene Glycol → HCID 178486627, compound

HRID 324022Notes

Reaction equation

[NH:1]([C:3]1[CH:8]=[C:7]([C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[CH:12]=[C:11]([CH2:23][OH:24])[C:10]=2[CH2:25][OH:26])[CH:6]=[CH:5][N:4]=1)[NH2:2].[C:27]1(=O)[O:32][C:30](=[O:31])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12.C(O)CO.C(Cl)Cl>O>[OH:32][C:27]1[C:28]2[C:29](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:30](=[O:31])[N:1]([C:3]2[CH:8]=[C:7]([C:9]3[C:18]4[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=4)[CH:12]=[C:11]([CH2:23][OH:24])[C:10]=3[CH2:25][OH:26])[CH:6]=[CH:5][N:4]=2)[N:2]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 1-(2-hydrazino-4-pyridyl)-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (2.0 g), phthalic anhydride (0.92 g) and ethylene glycol (10 ml) is heated with stirring at 130° C. for two hours. The mixture is cooled to room temperature, and thereto are added methylene chloride and water. The methylene chloride layer is separated, washed, dried, concentrated under reduced pressure to remove the solvent, and the residue is crystallized from ethanol to give 1-[2-{4-(hydroxy)-1(2H)-phthalazinon-2-yl}-4-pyridyl]-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (1.68 g, yield; 61%), which is listed in Table 10.

Workup

temperatureis heated
temperatureThe mixture is cooled to room temperature
customThe methylene chloride layer is separated
washwashed
customdried
concentrationconcentrated under reduced pressure
customto remove the solvent
customthe residue is crystallized from ethanol

Sources & evidence

ORD record: ord-517b0e150c434fcabbcca359ae02eca8
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06214996B1

Reaction notes

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