Phloroglucinol → HCID 10540475, compound

HRID 1595208Notes

Reaction equation

HRID 1595208 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 maintained at reflux using a Dean-Stark apparatus for 48 hours, with stirring, and the reaction mixture is then concentrated in vacuo. The residue is chromatographed on silica gel (eluant: cyclohexane/acetone: 90/10). The isolated product is crystallised from a cyclohexane/acetone mixture, yielding 5.2 g of the expected product.

Workup

  1. temperatureThe mixture is maintained
  2. temperatureat reflux
  3. customfor 48 hours
  4. concentrationthe reaction mixture is then concentrated in vacuo
  5. customThe residue is chromatographed on silica gel (eluant: cyclohexane/acetone: 90/10)
  6. customThe isolated product is crystallised from a cyclohexane/acetone mixture

Sources & evidence

ORD record
ord-0be4b1a6d833476cbdaa5e0894292c91
Source dataset
uspto-grants-2001_09
Patent number
US06288073B1

Reaction notes

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