Sodium Sulfide → 1-Amino-6,7-dimethylanthracene-9,10-dione

HRID 1658857Notes

Reaction equation

HRID 1658857 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:5]=1[C:6](=[O:21])[CH:7]1[CH:12]([C:13]2=[O:18])[CH2:11][C:10]([CH3:19])=[C:9]([CH3:20])[CH2:8]1)([O-])=O.[S-2].[Na+].[Na+]>O>[NH2:1][C:4]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:5]=1[C:6](=[O:21])[C:7]1[CH:8]=[C:9]([CH3:20])[C:10]([CH3:19])=[CH:11][C:12]=1[C:13]2=[O:18]

Participants

4

Reactant 2

HCID 14804Sodium SulfideHCID 212925545-Nitro-2,3-dimethyl-1,4,4a,9a-tetrahydroanthraquinone

Product 1

HCID 212925531-Amino-6,7-dimethylanthracene-9,10-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To 5.0 parts of 5-nitro-2,3-dimethyl-1,4,4a,9a-tetrahydroanthraquinone there was added 100 parts of water and then, with stirring at 90°C, 20 parts of a 10 wt % aqueous sodium sulfide. The reaction mixture thus formed was maintained at 90° - 95°C for 1 hour and, after cooled to 25°C, filtered to recover crystals. The crystals were washed with water and dried under reduced pressure to obtain 4.5 parts of 5-amino-2,3-dimethylanthraquinone of a melting point of 222°C.

Workup

  1. customThe reaction mixture thus formed
  2. temperaturewas maintained at 90° - 95°C for 1 hour
  3. temperatureafter cooled to 25°C
  4. filtrationfiltered
  5. customto recover crystals
  6. washThe crystals were washed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-c96ef66cab094f64a98d98346859743c
Source dataset
uspto-grants-1976_06
Patent number
US03966775

Reaction notes

Loading…