N,N-Dimethylethylenediamine → HCID 45377508, compound

HRID 1019482Notes

Reaction equation

HRID 1019482 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 Compound 1 as dark blue product. Abs (max, PBS pH 7.4)=568 nm; Em=675 nm. The structure of Compound 1 is given below:

Workup

  1. customAfter evaporation of the solvents
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-af840a28753544d781d0d4fc19ef5f8d
Source dataset
uspto-grants-2014_05
Patent number
US08715944B2

Reaction notes

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