N,N-Dimethylethylenediamine → HCID 45377508, compound

HRID 1773001Notes

Reaction equation

HRID 1773001 reaction equation
F[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([OH:18])[CH:10]=[CH:11][C:12]=3[OH:17])[C:7](=[O:19])[C:6]=2[C:5](F)=[C:4]([F:21])[C:3]=1[F:22].[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][NH2:27]>C(Cl)Cl>[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][NH:27][C:5]1[C:6]2[C:7](=[O:19])[C:8]3[C:13](=[C:12]([OH:17])[CH:11]=[CH:10][C:9]=3[OH:18])[C:14](=[O:16])[C:15]=2[C:2]([NH:27][CH2:26][CH2:25][N:24]([CH3:28])[CH3:23])=[C:3]([F:22])[C:4]=1[F:21]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 35272671,2,3,4-Tetrafluoro-5,8-dihydroxyanthraquinone

Product 1

HCID 45377508HCID 45377508, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,2,3,4-tetrafluoro-5,8-dihydroxyanthraquinone (1.0 g, 3.2 mmol) and N,N-dimethylethylenediamine (3 mL) in CH2Cl2 (30 mL) was stirred at room temperature for 12 hours. After evaporation of the solvents, the residue was purified by silica gel chromatography using isocratic solvent system of EtOAc/MeOH/Et3N (10:10:1) yielding 830 mgs of Dye 1 as dark blue product. Abs (max, PBS pH 7.4)=568 nm; Em=675 nm. The structure of Dye 1 is given below:

Workup

  1. customAfter evaporation of the solvents
  2. customthe residue was purified by silica gel chromatography
  3. customyielding 830 mgs of Dye 1 as dark blue product

Sources & evidence

ORD record
ord-c5db800468b34aaa8c0bd94d7855dc53
Source dataset
uspto-grants-2016_02
Patent number
US09250249B2

Reaction notes

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