Phloroglucinol → HCID 10540475, compound

HRID 478682Notes

Reaction equation

HRID 478682 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

5

Reactant 3

HCID 359PhloroglucinolHCID 6101p-Toluenesulfonic acidHCID 222443-Amino-2-naphthoic acid

Product 1

HCID 10540475HCID 10540475, compound

Reagents, catalysts & solvents 1

HCID 8129HeptanolSolvent

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.

Workup

  1. temperatureunder reflux
  2. concentrationthe reaction mixture is then 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
  5. customto be obtained

Sources & evidence

ORD record
ord-e4144cce5a6d4a16b18734d3fe869d9c
Source dataset
uspto-grants-2003_11
Patent number
US06642248B2

Reaction notes

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