Hydrogen Sulfide → 1-Aminoanthraquinone

HRID 1658856Notes

Reaction equation

HRID 1658856 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.N1C=CC=CC=1.S>O>[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 3

HCID 402Hydrogen SulfideHCID 1049PyridineHCID 108689405-Nitro-1,4,4a,9a-tetrahydroanthraquinone

Product 1

HCID 67101-Aminoanthraquinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5.0 parts of 5-nitro-1,4,4a,9a-tetrahydroanthraquinone with 50 parts of pyridine was stirred at 90°C for 2 hours with introducing thereinto 0.8 parts/hour of gaseous hydrogen sulfide. The reaction mixture was then cooled to 25°C and added with 50 parts of water to precipitate crystals. The crystals were recovered by filtration, washed with water and dried under reduced pressure to obtain 3.9 parts of 1-aminoanthraquinone.

Workup

  1. additionwith introducing
  2. temperatureThe reaction mixture was then cooled to 25°C
  3. customto precipitate crystals
  4. filtrationThe crystals were recovered by filtration
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-4446aae9b73848579356cfdb51b618b9
Source dataset
uspto-grants-1976_06
Patent number
US03966775

Reaction notes

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