1-Nitroanthraquinone → 1-Aminoanthraquinone

HRID 647030Notes

Reaction equation

HRID 647030 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.[S-2].[Na+].[Na+]>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

4

Reactant 2

HCID 67041-NitroanthraquinoneHCID 14804Sodium Sulfide

Product 1

HCID 67101-Aminoanthraquinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

10 parts of the nitroanthraquinone used in Example 1 was made pasty with 23.9 parts of sodium sulfide flakes (60% purity) and 11 parts of water, and this dark green paste was poured into 800 parts of hot water of 95°-98° C. and the remainder was poured by washing with 170 parts of cold water. This was followed by additional 2-hour agitation at 97°-100° C. The reaction mixture was then filtered at 70°-80° C., washed and dried to obtain 8.38 parts of an aminoanthraquinone with purity of 75.0%. The yield of 1-aminoanthraquinone was 96.0%. The aminoanthraquinone crystals mostly had the size of 1 to 2μ as shown in FIG. 4, but a part of the crystals had size of 5 to 10μ. Filterability of the product was very bad as in the case of Referential Examples 1 and 2.

Workup

  1. additionthe remainder was poured
  2. washby washing with 170 parts of cold water
  3. waitThis was followed by additional 2-hour agitation at 97°-100° C
  4. filtrationThe reaction mixture was then filtered at 70°-80° C.
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-6396a88814284c9bbe446ee763bcaf9b
Source dataset
uspto-grants-1983_10
Patent number
US04407756

Reaction notes

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