4-(Aminomethyl)cyclohexanecarboxylic acid → Coumarin

HRID 1899756Notes

Reaction equation

HRID 1899756 reaction equation
O.CO.CN([C:7]1[CH:12]=[CH:11][C:10]2[C:13]3CCC[C:14]=3[C:18]([O:20][C:9]=2[CH:8]=1)=[O:19])C.CCOC(C1C(=O)OC2C(=CC3CCCN4C=3C=2CCC4)C=1)=O.C1C(CN)CCC(C(O)=O)C1>ClCCl.C(O)C>[O:20]1[C:9]2[C:10](=[CH:11][CH:12]=[CH:7][CH:8]=2)[CH:13]=[CH:14][C:18]1=[O:19]

Participants

7

Reactant 4

HCID 55264-(Aminomethyl)cyclohexanecarboxylic acidHCID 72653Coumarin 3143×HCID 100527Cyclopenta[c][1]benzopyran-4(1H)-one, 7-(dimethylamino)-2,3-dihydro-3×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.; 2.75% solids in 50% v/v distilled water/methanol) is added a solution of 30 mg of Coumarin 138 (Eastman Kodak, Rochester, N.Y.) and 30 mg of Coumarin 314 (Eastman Kodak) dissolved in a homogeneous mixture of 7.5 mL of dichloromethane and 17.5 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 AMCA excitation and emission filters shows uniformly dyed particles that are highly monodisperse. Spectral analysis of the product, exciting at 360 nm shows an emission peak centered at 410 nm and an emission peak centered at 460 nm. The integrated ratio of the 460 nm peak (from coumarin 314) to the 410 peak (from coumarin 138) is 92:8, indicating efficient transfer of emission energy from coumarin 138 to coumarin 314.

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-7ad6a76708284737bf19a6453ca7843c
Source dataset
uspto-grants-1996_11
Patent number
US05573909

Reaction notes

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