P-Anisidine → 1-p-Anisidino-8-nitro-anthraquinone

HRID 1729570Notes

Reaction equation

HRID 1729570 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-:21])=[O:20])[C:9](=[O:22])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28](N)=[CH:27][CH:26]=1.C([O-])(=O)C.[K+]>CO>[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([NH:1][C:4]2[C:17]3[C:16](=[O:18])[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][C:14]=4[N+:19]([O-:21])=[O:20])[C:9](=[O:22])[C:8]=3[CH:7]=[CH:6][CH:5]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 672101,8-Dinitro-9,10-anthraquinoneHCID 517044Potassium Acetate

Product 1

HCID 203164861-p-Anisidino-8-nitro-anthraquinoneYield 81.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 50 g of 1,8-dinitro-anthraquinone (82% strength), 150 g of p-anisidine and 21.5 g of anhydrous potassium acetate is heated at 95° - 100° C (duration approx. 5 hours), with vigorous stirring, until no further starting material is present, according to thin layer chromatography. The mixture is diluted with 150 ml of methanol over the course of 30 minutes at 50° - 60° C and is stirred overnight until cold and the reaction product is filtered off, washed with a solution of 30 g of p-anisidine in 30 ml of methanol and finally with 200 ml of methanol and hot water, and dried at 80° C. 51 g of 1-p-anisidino-8-nitro-anthraquinone are obtained.

Workup

  1. temperatureis heated at 95° - 100° C (duration approx. 5 hours)
  2. filtrationis filtered off
  3. washwashed with a solution of 30 g of p-anisidine in 30 ml of methanol and finally with 200 ml of methanol and hot water
  4. customdried at 80° C

Sources & evidence

ORD record
ord-0bba9ba4652b4da69abc6bf80b5393bb
Source dataset
uspto-grants-1976_11
Patent number
US03989450

Reaction notes

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