1-Nitroanthraquinone → 1-Aminoanthraquinone

HRID 1658846Notes

Reaction equation

HRID 1658846 reaction equation
C1(OC)C=CC=CC=1.[N+:9]([C:12]1[C:25]2[C:24](=[O:26])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:27])[C:16]=2[CH:15]=[CH:14][CH:13]=1)([O-])=O.[H][H].ONC1C2C(=O)C3C(=CC=CC=3)C(=O)C=2C=CC=1>[Pd]>[NH2:9][C:12]1[C:25]2[C:24](=[O:26])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:27])[C:16]=2[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 67041-NitroanthraquinoneHCID 7519AnisoleHCID 178418361HCID 178418361, compound3×HCID 178514954HCID 178514954, compound

Product 1

HCID 67101-AminoanthraquinoneYield 97%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

300 Parts by weight of anisole are mixed with 27 parts of (97%) 1-nitroanthraquinone and 0.2 parts by weight of a palladium/charcoal catalyst (5% of Pd on active charcoal) and heated to 130° in an autoclave. At this temperature, hydrogen is blown through until the rate of up-take of the hydrogen has fallen to 10% of the original value. At this stage, about 2% of overhydrogenation product is present (ascertained by TLC). After interruption of the hydrogen supply, at 130°, 0.4 parts by weight of 1-hydroxylaminoanthraquinone are added and stirring is effected for 30 minutes. The catalyst is separated off at the upper temperature, the filtrate is concentrated and cooled and the 1-aminoanthraquinone is filtered off. No nuclear hydrogenated 1-aminoanthraquinone is present in the mother liquor. 23 Parts of 97% pure 1-aminoanthraquinone is obtained.

Workup

  1. temperatureheated to 130° in an autoclave
  2. customThe catalyst is separated off at the upper temperature
  3. concentrationthe filtrate is concentrated
  4. temperaturecooled
  5. filtrationthe 1-aminoanthraquinone is filtered off

Sources & evidence

ORD record
ord-d7d4a0b142d3488c9fbcb1e21e30c0ce
Source dataset
uspto-grants-1976_06
Patent number
US03966774

Reaction notes

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