Acetic Acid → 1-Aminoanthraquinone

HRID 654570Notes

Reaction equation

HRID 654570 reaction equation
C[N:2]1[CH2:6][CH2:5][CH2:4][C:3]1=[O:7].N1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=CC=1.C(O)(=[O:20])C.N1C=C[CH:25]=[CH:24][CH:23]=1>[Cu]>[NH2:2][C:6]1[C:5]2[C:11](=[O:20])[C:12]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:3](=[O:7])[C:4]=2[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1049Pyridine3×HCID 7047QuinolineHCID 13387N-methyl-2-pyrrolidone

Product 1

HCID 67101-AminoanthraquinoneYield 64%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

Process conditions and product yields are shown in Table IV. The decarboxylation of 1-AAQCA was carried out in several solvents, e.g., N-methylpyrrolidone, pyridine, quinoline and acetic acid. The best results were obtained in pyridine. When decarboxylation of 1-AAQCA was carried out with 5 mol % of copper powder in pyridine at 260° C. for 2.5 hours, complete conversion was observed. Distillation of the crude product afforded 1-aminoanthraquinone (1-AAQ) in 64% yield. We were unable to decarboxylate 1-AAQCA in pyridine alone, without a copper catalyst. Decarboxylation of 1-AAQCA in quinoline using 5 mol % of copper powder gave 1-AAQ in 65% yield.

Workup

  1. customProcess conditions and product yields
  2. customThe best results
  3. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-7c6a85546495470794ea93096b5be157
Source dataset
uspto-grants-1992_07
Patent number
US05132437

Reaction notes

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