Putrescine → 1-(4-Aminobutylamino)-4-methoxyanthracene-9,10-dione

HRID 330060

Reaction equation

HRID 330060 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].[CH3:7][O:8][C:9]1[C:22]2[C:21](=[O:23])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:24])[C:13]=2[C:12](OC)=[CH:11][CH:10]=1>C(Cl)Cl>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:12]1[C:13]2[C:14](=[O:24])[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21](=[O:23])[C:22]=2[C:9]([O:8][CH3:7])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 1045PutrescineHCID 2660541,4-Dimethoxyanthraquinone

Product 1

HCID 133805781-(4-Aminobutylamino)-4-methoxyanthracene-9,10-dioneYield 50.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,4-Diaminobutane (1.65 g, 19 mmol) was added to a solution of 1,4-dimethoxyanthracene-9,10-dione (1.0 g, 3.7 mmol) in CH2Cl2 (700 ml). After seven, hours of irradiation, the solvent was removed and the residue chromatographed on silica gel. Starting material was eluted with CHCl3 and the product with 5% CH3OH in CHCl3. A purple solid (0.61 g, 50%) was obtained which was converted to the benzyloxycarbonyl derivative.

Workup

  1. customAfter seven, hours of irradiation
  2. customthe solvent was removed
  3. customthe residue chromatographed on silica gel
  4. washStarting material was eluted with CHCl3

Sources & evidence

ORD record
ord-cb9650b945854228a55b0887a0509362
Source dataset
uspto-grants-1990_01
Patent number
US04894451

Linked notes

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