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Sodium Hydroxide → 1,8-Diamino-9,10-anthracenedione

HRID 556196
Notes
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Reaction equation

HRID 556196 reaction equation
ClCC([NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[NH:21]C(=O)CCl)[C:11](=[O:26])[C:10]=2[CH:9]=[CH:8][CH:7]=1)=O.[N+](C1C2C(=O)C3C(=CC=CC=3[N+]([O-])=O)C(=O)C=2C=CC=1)([O-])=O.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].[OH-].[Na+]>C(O)C>[NH2:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[NH2:21])[C:11](=[O:26])[C:10]=2[CH:9]=[CH:8][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 672101,8-Dinitro-9,10-anthraquinoneHCID 73972Sodium sulfide nonahydrateHCID 469280411,8-Bis(chloroacetamido)anthraquinone

Product 1

HCID 85111,8-Diamino-9,10-anthracenedione

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

In the step S1, a manufacturing method of 1,8-bis(chloroacetamido)anthraquinone includes the steps of: add 1,8-dinitroanthraquinone with ethanol, and then add sodium sulfide nonahydrate and sodium hydroxide solution into the mixture to be mixed and reflux heated. After standing and filtration, 1,8-diaminoanthraquinone is obtained by recrystallization of the solution. Next the 1,8-diaminoanthraquinone is dissolved in N,N-dimethylform amide, and pyridine is added for catalyzing, and then chloroacetyl chloride is added into and mixed with the mixture to react. Pour the solution into ice water, 1,8-bis(chloroacetamido) anthraquinone is obtained after filtration and recrystallization of the solution. The step of adding pyridine for catalyzing is run under an ice-bath while in the step of adding and mixing chloroacetyl chloride into the mixture, the ice bath is removed, the nitrogen gas is introduce and the step is run under light protection condition. The step of adding and mixing chloroacetyl chloride into the mixture is run at the room temperature for 24 hours.

Workup

  1. temperaturereflux
  2. temperatureheated
  3. filtrationfiltration

Sources & evidence

ORD record
ord-41fb87150f0247df9b854dce5420b4c7
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08053583B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes