Phloroglucinol → HCID 10540475, compound

Reaction equation

[NH2:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[OH:15][C:16]1[CH:21]=[C:20](O)[CH:19]=[C:18]([OH:23])[CH:17]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)CCCCCC>[OH:15][C:16]1[C:21]2[C:12](=[O:14])[C:3]3[CH:4]=[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:10]4=[CH:11][C:2]=3[NH:1][C:20]=2[CH:19]=[C:18]([OH:23])[CH:17]=1

Participants

Procedure

To a solution of 5 g of 3-amino-2-naphthalenecarboxylic acid in 50 ml of heptan-1-ol there are added 3.5 g of 1,3,5-trihydroxybenzene and 62.5 mg of para-toluenesulphonic acid. The mixture is stirred for 48 hours under reflux using a Dean-Stark apparatus, and the reaction mixture is then concentrated in vacuo. The residue is chromatographed over silica gel (eluant: cyclohexane/acetone: 90/10). The isolated product is crystallised from a cyclohexane/acetone mixture, allowing 5.2 g of the expected product to be obtained.