4-{2,2-Bis[4-(dimethylamino)phenyl]ethenyl}naphthalene-1,2-dione → HCID 19388532, compound

HRID 1757515Notes

Reaction equation

HRID 1757515 reaction equation
[C:1]1(=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=[C:12]([C:22]2[CH:27]=[CH:26][C:25]([N:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=2)[C:13]2[CH:18]=[CH:17][C:16]([N:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=2)=[CH:3][C:2]1=[O:31].Cl.[NH2:34][OH:35]>C(O)C>[N:34]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=[C:12]([C:13]2[CH:14]=[CH:15][C:16]([N:19]([CH3:20])[CH3:21])=[CH:17][CH:18]=2)[C:22]2[CH:27]=[CH:26][C:25]([N:28]([CH3:29])[CH3:30])=[CH:24][CH:23]=2)=[CH:3][C:2]=1[OH:31])=[O:35]

Participants

4

Reactant 2

HCID 2922264-{2,2-Bis[4-(dimethylamino)phenyl]ethenyl}naphthalene-1,2-dioneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 19388532HCID 19388532, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(1,2-naphthoquinon-4-yl)-1,1-bis(p-dimethylaminophenyl)ethylene (1.63 g; 0.004 mol) was dissolved in absolute ethanol (100 ml) by warming. To the solution, at room temperature, was added hydroxylamine hydrochloride (3.7 g;0.053 mol) and the resulting solution was stirred for 5 hours. The mixture was then evaporated to dryness treated with water and extracted with CH2Cl2. The organic extract was dried, evaporated to dryness and then chromatographed over silica (eluent:diethyl ether) to afford 2-(1-nitroso-2-hydroxynaphthalen-4-yl)-1,1-bis(p-dimethylamin ophenyl)ethylene (0.83 g;49%) as a dark brown solid.

Workup

  1. temperatureby warming
  2. customThe mixture was then evaporated to dryness
  3. additiontreated with water
  4. extractionextracted with CH2Cl2
  5. extractionThe organic extract
  6. customwas dried
  7. customevaporated to dryness
  8. customchromatographed over silica (eluent:diethyl ether)

Sources & evidence

ORD record
ord-0549463b151349d89f7cdae4c66661ca
Source dataset
uspto-grants-1995_08
Patent number
US05446150

Reaction notes

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