Methanol → 1-Aminoanthraquinone

HRID 1658862Notes

Reaction equation

HRID 1658862 reaction equation
O[NH:2][C:3]1[C:16]2[C:15](=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1.CO.COCCOCCO.S(=O)(=O)(O)O>[Zn].O>[NH2:2][C:3]1[C:16]2[C:15](=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 8134Diethylene Glycol Monomethyl EtherHCID 178514954HCID 178514954, compound

Product 1

HCID 67101-Aminoanthraquinone

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

50 Parts of 1-hydroxylaminoanthraquinone was stirred into a mixture of 700 parts of diethyleneglycol monomethyl ether, 100 parts of water and 30 parts of conc. sulfuric acid, then added thereto little by little 16 parts of zinc dust over 1 hour after heating to 80°C. The reaction mixture was maintained at 80°C for additional 2 hours and then filtered. The filtrate was washed with water and dried to obtain 43.5 parts of 1-aminoanthraquinone of a purity of 94 %.

Workup

  1. additionadded
  2. filtrationfiltered
  3. washThe filtrate was washed with water
  4. customdried

Sources & evidence

ORD record
ord-70537515cff24428a4931545db3911de
Source dataset
uspto-grants-1976_06
Patent number
US03966775

Reaction notes

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