Oxalic Acid → 1,4-Dihydronaphtho[2,3-f]quinoxaline-2,3,7,12-tetrone

HRID 2093357Notes

Reaction equation

HRID 2093357 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].[C:19](O)(=[O:23])[C:20](O)=[O:21].S(=O)(=O)(O)O>CN(C)C=O>[NH:1]1[C:2]2[C:15]3[C:14](=[O:16])[C:13]4[C:8]([C:7](=[O:17])[C:6]=3[CH:5]=[CH:4][C:3]=2[NH:18][C:20](=[O:21])[C:19]1=[O:23])=[CH:9][CH:10]=[CH:11][CH:12]=4

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 1118Sulfuric AcidHCID 156521,2-Diaminoanthraquinone

Product 1

HCID 442512911,4-Dihydronaphtho[2,3-f]quinoxaline-2,3,7,12-tetrone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2-Diaminoanthraquinone (1.19 g, 5 mmol) is dissolved in N,N-dimethylformamide (30 mL), and oxalic acid (0.46 g, 5 mmol) and concentrated sulfuric acid (0.1 mL) is added thereinto. After reverse flow for 16 hours, the reacted mixture is transferred into icy water (200 mL) for precipitation. The precipitate is collected and washed by hot alcohol and, so as to obtain the black compound 26, and the production rate is 30%.

Workup

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

Sources & evidence

ORD record
ord-f3a139ed37144deeb40f96b6f4485f60
Source dataset
uspto-grants-2013_05
Patent number
US08445492B2

Reaction notes

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