9,10-Phenanthrenedione → 10-(3,6-Dimethyl-2-pyrazinylazo)-9-phenanthrol

HRID 1266916

Reaction equation

[CH:1]1[C:14]2[C:13](=O)[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH:17]([C:19]1[C:24]([CH3:25])=[N:23][CH:22]=[C:21]([CH3:26])[N:20]=1)[NH2:18]>C(O)(=O)C>[CH3:25][C:24]1[C:19]([N:17]=[N:18][C:13]2[C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[OH:16])=[N:20][C:21]([CH3:26])=[CH:22][N:23]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Next, a reaction flask was loaded with acetic acid (80 ml) and 9,10-phenanthrenequinone (4.0 g), and heated up to 90° C. with stirring to dissolve 9,10-phenanthrenequinone. To the resultant, the crystals of 2-hydrazino-3,6-dimethylpyrazine (2.7 g) was added in 20 minutes. After stirring at 90 to 100° C. for two hours, the reaction mixture was cooled and filtrated. An aqueous solution of sodium hydroxide was added to the filtrate with stirring so that crystals precipitated. The crystals were filtrated and washed with methanol, followed by being recrystallized with dioxane-water. The crystals were then filtrated and dried to give intended crystals (3.3 g).

Workup

stirringAfter stirring at 90 to 100° C. for two hours
temperaturethe reaction mixture was cooled
filtrationfiltrated
additionAn aqueous solution of sodium hydroxide was added to the filtrate
stirringwith stirring so that crystals
customprecipitated
filtrationThe crystals were filtrated
washwashed with methanol
customby being recrystallized with dioxane-water
filtrationThe crystals were then filtrated
customdried
customto give

Sources & evidence

ORD record: ord-22d9b89bb7dd4e698e3b7fa6fb54a52c
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06551682B1

Linked notes

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