Methanol → 1-Amino-5-methoxyanthracene-9,10-dione

HRID 918541Notes

Reaction equation

HRID 918541 reaction equation
[CH3:1][OH:2].[OH-].[Na+].[NH2:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[CH:16]=[CH:15][CH:14]=[C:13](S(O)(=O)=O)[C:12]=3[C:11](=[O:25])[C:10]=2[CH:9]=[CH:8][CH:7]=1>O>[NH2:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[C:13]([O:2][CH3:1])[CH:14]=[CH:15][CH:16]=3)[C:11](=[O:25])[C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 777241-Aminoanthraquinone-5-sulfonic acid

Product 1

HCID 138979031-Amino-5-methoxyanthracene-9,10-dioneYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

40 parts by volume of methanol and 10 parts of sodium hydroxide are dissolved at the boil and 13.3 parts of 1-aminoanthraquinone-5-sulphonic acid are introduced into this solution at 80°C, over the course of 30 minutes, with vigorous stirring. The mixture is now stirred for a further 3 hours at 80°-85°C until only traces of starting material are still present according to chromatography. The mixture is now diluted with 50 parts of hot water and the product is filtered off, washed with boiling hot water until neutral and dried at 100°-120°C. 8.9 parts of 1-amino-5-methoxy-anthraquinone (80% of theory) are obtained.

Workup

  1. additionare introduced into this solution at 80°C, over the course of 30 minutes, with vigorous stirring
  2. filtrationthe product is filtered off
  3. washwashed
  4. customdried at 100°-120°C

Sources & evidence

ORD record
ord-0844405c41a84152bbc8c1bc3c291af8
Source dataset
uspto-grants-1976_07
Patent number
US03971812

Reaction notes

Loading…