Ethanol → 1,8-Diamino-9,10-anthracenedione

HRID 556197

Reaction equation

HRID 556197 reaction equation
[N+:1]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[N+:19]([O-])=O)[C:9](=[O:22])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.C(O)C.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].[OH-].[Na+]>O>[NH2:1][C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[NH2:19])[C:9](=[O:22])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 672101,8-Dinitro-9,10-anthraquinoneHCID 73972Sodium sulfide nonahydrate

Product 1

HCID 85111,8-Diamino-9,10-anthracenedioneYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 1,8-dinitroanthraquinone (1.49 g, 5 mmol) into 56 ml ethanol and stir the mixture. Then add a reductive solution containing sodium sulfide nonahydrate (5.4 g, 22.5 mmol), sodium hydroxide (2.14 g, 53.5 mmol) dissolved in 95 ml water. The mixed solution is reflux heated for 6 hours, standing overnight, and filter the precipitate. The precipitate is recrystallized from ethanol to get red compound 2.

Workup

  1. additionThen add a reductive solution
  2. temperatureThe mixed solution is reflux
  3. temperatureheated for 6 hours
  4. filtrationfilter the precipitate
  5. customThe precipitate is recrystallized from ethanol

Sources & evidence

ORD record
ord-16649f51f64d4d918c01e5cc076fcec2
Source dataset
uspto-grants-2011_11
Patent number
US08053583B2

Linked notes

Loading…