2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid → Coumarin

HRID 1899757Notes

Reaction equation

HRID 1899757 reaction equation
O.CO.CCN([C:9]1[CH:14]=[CH:13][C:12]2[CH:15]=[C:16](C3SC4C(=CC=CC=4)N=3)[C:17]([O:19][C:11]=2[CH:10]=1)=[O:18])CC.C1C=CC(C(O)=O)=C(C2C3C=CC(O)=CC=3OC3C=2C=CC(C=3)=O)C=1>ClCCl.C(O)C>[O:19]1[C:11]2[C:12](=[CH:13][CH:14]=[CH:9][CH:10]=2)[CH:15]=[CH:16][C:17]1=[O:18]

Participants

6

Reactant 3

HCID 33832-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acidHCID 100334Coumarin 62×HCID 22242641Methanol--water (1/1)

Product 1

HCID 323Coumarin

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a vigorously stirred 200 mL suspension 0.282 micrometer carboxylate-modified latex (Interfacial Dynamics Corp., Portland, Oreg.; 2.10% solids in 50% v/v distilled water/methanol) is added a solution of 50 mg of coumarin 6 and 50 mg of Compound 1 dissolved in a homogeneous mixture of 9 mL of dichloromethane and 16 mL of absolute ethanol. The addition of the dye and purification of the product is carried out as described in EXAMPLE 3. Visual analysis of a dilute aqueous suspension of the product by fluorescence microscopy using standard fluorescein excitation and emission filters shows uniformly dyed particles that are highly monodisperse. Spectral analysis of the product, exciting at 430 nm shows the major emission peak to be centered at 512 nm. There is a smaller emission peak centered at 520 nm from the coumarin 6, indicating substantial, but not complete energy transfer.

Workup

  1. additionThe addition of the dye and purification of the product
  2. additionVisual analysis of a dilute aqueous suspension of the product by fluorescence microscopy

Sources & evidence

ORD record
ord-3af19ac10723444aa2694216420580a1
Source dataset
uspto-grants-1996_11
Patent number
US05573909

Reaction notes

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