1-Nitroanthraquinone → 1-dimethylaminoanthraquinone

HRID 442048Notes

Reaction equation

HRID 442048 reaction equation
[N+]([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.CN(C)P(=O)([N:26]([CH3:28])[CH3:27])N(C)C>O>[CH3:27][N:26]([CH3:28])[C:11]1[C:10]2[C:9](=[O:19])[C:8]3[C:17](=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:16](=[O:18])[C:15]=2[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 67041-NitroanthraquinoneHCID 12679Hexamethylphosphoramide

Product 1

HCID 28402061-dimethylaminoanthraquinoneYield 92.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

25.3 parts of 1-nitroanthraquinone and 227 parts of hexamethylphosphoric triamide are heated in an agitator flask for 4 hours to 180° C and for 11/2 hours to 210° C. After it has been cooled, the reaction mixture is poured into 1000 parts of water. The precipitated product is collected by filtration, washed with water and dried, to yield 23.2 parts (=92.4% of theory) of 1-dimethylaminoanthraquinone.

Workup

  1. temperatureAfter it has been cooled
  2. filtrationThe precipitated product is collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-d96da33a36b24121abc758dc5c619825
Source dataset
uspto-grants-1977_08
Patent number
US04044030

Reaction notes

Loading…