Water → 4-(4-(Ethyl(2-hydroxyethyl)amino)phenyl)naphthalene-1,2-dione

HRID 537633Notes

Reaction equation

[Na+].[C:2]1(=[O:17])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](S([O-])(=O)=O)=[CH:4][C:3]1=[O:16].O.[CH2:19]([N:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:22][CH2:23][OH:24])[CH3:20]>CO>[CH2:19]([N:21]([CH2:22][CH2:23][OH:24])[C:25]1[CH:26]=[CH:27][C:28]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2](=[O:17])[C:3](=[O:16])[CH:4]=2)=[CH:29][CH:30]=1)[CH3:20]

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 1,2-napthoquinone-4-sulfonic acid sodium salt (10.5 g, 40.35 mmol) in a 9:1 mixture of water:MeOH (250 ml) was treated in one portion with 2-(ethyl(phenyl)amino)ethanol (6.67 g, 40.35 mmol) and stirred at 50° C. for 18 hrs. The mixture was then cooled, the MeOH removed in vacuo and the resulting suspension filtered. The precipitate was then washed with water and oven dried at 50° C. to give the product, 4-(4-(ethyl(2-hydroxyethyl)amino)phenyl)naphthalene-1,2-dione, as a dark purple solid (6.8 g, 54%). Analysis of the product by 1H NMR gave a spectrum consistent with the structure.

Workup

temperatureThe mixture was then cooled
customthe MeOH removed in vacuo
filtrationthe resulting suspension filtered
washThe precipitate was then washed with water and oven
customdried at 50° C.

Sources & evidence

ORD record: ord-d6bcc96935a14d4ba6f7c1aa61bfe900
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865029B2

Reaction notes

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