1-Nitroanthraquinone → 1-Aminoanthraquinone

HRID 2057875Notes

Reaction equation

HRID 2057875 reaction equation
[N+:1]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>[N+](C1C=CC=CC=1)([O-])=O>[NH2:1][C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 67041-Nitroanthraquinone

Product 1

HCID 67101-AminoanthraquinoneYield 100.6%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
180 °C

Procedure

85 g of 1-nitro-anthraquinone, redissolved in nitrobenzene and reprecipitated (88.2% pure), is heated to 180° C. with 145 ml of water in a 0.7 l stirred autoclave. A solution of 14.6 g of NH4Cl in 240 ml of 25% strength NH3 solution is pumped in over a period of 5 minutes. The mixture is allowed to react for a further hour and cooled and the product is filtered off. After drying, 75.4 g of 86.8% pure 1-amino-anthraquinone=97.4% of theory are obtained.

Workup

  1. customreprecipitated (88.2% pure)
  2. customis pumped in over a period of 5 minutes
  3. customto react for a further hour
  4. temperaturecooled
  5. filtrationthe product is filtered off
  6. customAfter drying

Sources & evidence

ORD record
ord-16651a5476404c209c62d71f310dbf18
Source dataset
uspto-grants-1980_07
Patent number
US04213909

Reaction notes

Loading…