Water → 1-Nitroanthraquinone

HRID 2397261Notes

Reaction equation

HRID 2397261 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-:3])=[O:2].N[C:21]1[C:34]2[C:33](=[O:35])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26](=[O:36])[C:25]=2[CH:24]=[CH:23][CH:22]=1.[S-2].[K+].[K+].[OH2:40]>>[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.[OH:40][C:21]1[C:34]2[C:33](=[O:35])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26](=[O:36])[C:25]=2[CH:24]=[CH:23][C:22]=1[NH2:1].[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-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 67041-Nitroanthraquinone2×HCID 67101-AminoanthraquinoneHCID 162263Potassium Sulfide

Product 3

HCID 67041-NitroanthraquinoneHCID 67101-AminoanthraquinoneHCID 15570414HCID 15570414, compound

Procedure

The manufacture of 1-aminoanthraquinones by the reduction of 1-nitroanthraquinone has already been described. Beisler, Jones, Am. Soc. 44, 2304, were able to reduce 1-nitroanthraquinone to 1-aminoanthraquinone by treatment with potassium sulphide in boiling water. On the other hand, 1-aminoanthraquinone and 1-hydroxy-aminoanthraquinone result side by side in the reduction of 1-nitroanthraquinone dissolved in benzene with NaHS in an aqueous calcium chloride solution (Haworth, Lapworth, Soc. 119, 774).

Sources & evidence

ORD record
ord-baf9f6bdfc7942029d1235f89efd9d45
Source dataset
uspto-grants-1977_05
Patent number
US04021456

Reaction notes

Loading…