Sodium Hydroxide → 1-Aminoanthraquinone

HRID 1658854Notes

Reaction equation

HRID 1658854 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:5]=1[C:6](=[O:19])[CH:7]1[CH:12]([C:13]2=[O:18])[CH2:11][CH:10]=[CH:9][CH2:8]1)([O-])=O.[OH-].[Na+]>[Zn].C(O)C>[NH2:1][C:4]1[C:5]2[C:6](=[O:19])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13](=[O:18])[C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 108689405-Nitro-1,4,4a,9a-tetrahydroanthraquinone

Product 1

HCID 67101-Aminoanthraquinone

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 5.0 parts of 5-nitro-1,4,4a,9a-tetrahydroanthraquinone with 3 parts of zinc dust, 10 parts of a 20 wt % aqueous sodium hydroxide and 50 parts of ethanol was refluxed for 2 hours with stirring and, after cooled to 20°C, filtered. The residue was washed with water and poured into a dilute hydrochloric acid to dissolve zinc dust. Crystals were recovered by filration, washed with water and dried under reduced pressure to obtain 3.8 parts of 1-aminoanthraquinone.

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationfiltered
  3. washThe residue was washed with water
  4. additionpoured into a dilute hydrochloric acid
  5. dissolutionto dissolve zinc dust
  6. customCrystals were recovered by filration
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-6129ed43f30842c48e6f1d42a3543ba5
Source dataset
uspto-grants-1976_06
Patent number
US03966775

Reaction notes

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