Phloroglucinol → HCID 10540475, compound

HRID 1633527Notes

Reaction equation

HRID 1633527 reaction equation
O[C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([OH:9])[CH:3]=1.[NH2:10][C:11]1[C:12]([C:21](O)=[O:22])=[CH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2>C(O)CCCCCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:8][C:6]1[C:7]2[C:21](=[O:22])[C:12]3[CH:13]=[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]4=[CH:20][C:11]=3[NH:10][C:2]=2[CH:3]=[C:4]([OH:9])[CH:5]=1

Participants

5

Reactant 2

HCID 359PhloroglucinolHCID 222443-Amino-2-naphthoic acid

Product 1

HCID 10540475HCID 10540475, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8129HeptanolSolvent

Procedure

3.5 g of 1,3,5-trihydroxybenzene and 62.5 mg of para-toluenesulphonic acid are added to a solution of 5 g of 3-amino-2-naphthalenecarboxylic acid in 50 ml of heptan-1-ol. The mixture is stirred for 48 hours at reflux using a Dean Stark apparatus, and then the reaction mixture is 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 and yields 5.2 g of the expected product.

Workup

  1. temperatureat reflux
  2. concentrationthe reaction mixture is concentrated in vacuo
  3. customThe residue is chromatographed over silica gel (eluant: cyclohexane/acetone: 90/10)
  4. customThe isolated product is crystallised from a cyclohexane/acetone mixture

Sources & evidence

ORD record
ord-4aaa3d9314e64f409ec2b059ed615995
Source dataset
uspto-grants-2003_01
Patent number
US06503919B1

Reaction notes

Loading…