Sulfuric Acid → 2,3-Dimethylnaphtho[2,3-f]quinoxaline-7,12-dione

HRID 2093356Notes

Reaction equation

HRID 2093356 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:18].S(=O)(=O)(O)O.[CH:24]([C:26]([CH3:28])=O)=[CH2:25]>CN(C)C=O>[CH3:25][C:24]1[C:26]([CH3:28])=[N:18][C:3]2[CH:4]=[CH:5][C:6]3[C:7](=[O:17])[C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:14](=[O:16])[C:15]=3[C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6570Methyl vinyl ketoneHCID 156521,2-Diaminoanthraquinone

Product 1

HCID 442512902,3-Dimethylnaphtho[2,3-f]quinoxaline-7,12-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2-Diaminoanthraquinone (1.19 g, 5 mmol) is dissolved in N,N-dimethylformamide (30 mL), and concentrated sulfuric acid (0.1 mL) is further added thereinto after methyl vinyl ketone (0.36 g, 5 mmol) is added thereinto. After mixing and reacting in room temperature for 72 hours, the reacted mixture is transferred into icy water (200 mL) for precipitation. The precipitate is collected and recrystallized by hot alcohol, so as to obtain the black compound 24, and the production rate is 25%.

Workup

  1. additionAfter mixing
  2. customthe reacted mixture is transferred into icy water (200 mL) for precipitation
  3. customThe precipitate is collected
  4. customrecrystallized by hot alcohol

Sources & evidence

ORD record
ord-c7d0f797b3854e0093b942c946dd1e78
Source dataset
uspto-grants-2013_05
Patent number
US08445492B2

Reaction notes

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