Toluene → 1,5-Diamino-6-methyl-2-anthraquinonecarboxylic acid p-heptylphenyl ester

HRID 65177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 65177
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([C:17]2[CH:30]=[CH:29][C:28]3[C:27](=[O:31])[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([CH3:35])[C:25]=4[N+:32]([O-])=O)[C:20](=[O:36])[C:19]=3[C:18]=2[NH2:37])=[O:16])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C1(C)C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]([C:17]2[CH:30]=[CH:29][C:28]3[C:27](=[O:31])[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([CH3:35])[C:25]=4[NH2:32])[C:20](=[O:36])[C:19]=3[C:18]=2[NH2:37])=[O:16])=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Komponenten

6

Edukt 3

HCID 1140TolueneHCID 54519986HCID 54519986, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 540343611,5-Diamino-6-methyl-2-anthraquinonecarboxylic acid p-heptylphenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of 0.426 g of 1-amino-6-methyl-5-nitro-2-anthraquinonecarboxylic acid p-heptylphenyl ester, 50 ml of toluene, 50 ml of ethanol and 0.10 g of palladium/barium carbonate catalyst poisoned with 2 wt.% lead was hydrogenated at room temperature until the hydrogen uptake came to a standstill. The mixture was filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica gel with methylene chloride as the eluent. Recrystallization from methylene chloride/hexane, yielded 0.334 of 1,5-diamino-6-methyl-2-anthraquinonecarboxylic acid p-heptylphenyl ester as violet crystals; m.p. (C-N) 163.7°-165.7° C., cl.p. (N-I) 190.9°-191.4° C., nematic; E277 =15280, E524 =14700.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified by chromatography on silica gel with methylene chloride as the eluent
  4. customRecrystallization from methylene chloride/hexane

Quellen und Nachweise

ORD-Eintrag
ord-214e9e825054420aa86fb83ded385f06
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04613208

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