1,2-Naphthoquinone → Benzo[a]phenazine-11-carboxylic acid

HRID 719178

Reaktionsgleichung

Reaktionsgleichung von HRID 719178
[C:1]1(=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]1=O.C(O)(=O)C.C(O)(=O)C.[NH2:21][C:22]1[C:30]([NH2:31])=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([OH:26])=[O:25].C1C2=C3C(=CC=C2C=CC=1)N=C1C(C=CC=C1C(O)=O)=N3>C(O)(=O)C>[CH:9]1[C:10]2=[C:1]3[C:2](=[CH:3][CH:4]=[C:5]2[CH:6]=[CH:7][CH:8]=1)[N:31]=[C:30]1[C:22]([C:23]([C:24]([OH:26])=[O:25])=[CH:27][CH:28]=[CH:29]1)=[N:21]3

Komponenten

5

Edukt 3

HCID 106671,2-NaphthoquinoneHCID 13792240Benzo[a]phenazine-8-carboxylic acidHCID 857879142,3-Diamino-benzoic acid, diacetate salt

Produkt 1

HCID 13792239Benzo[a]phenazine-11-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 1,2-naphthoquinone (commercially available, 2.0 g) and 2,3-diamino-benzoic acid, diacetate salt, (3.79 g) was heated to reflux in acetic acid (30 mL) for 2 hours. The reaction mixture was cooled and the solvent removed in vacuo to yield a gum. This was purified using flash chromatography to yield a 2:1 mixture of the desired title compound to the undesired benzo[a]phenazine-8-carboxylic acid (840 mg). The two isomers were separated after further modification (see Reference Example 3B below).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent removed in vacuo
  4. customto yield a gum
  5. customThis was purified
  6. customto yield

Quellen und Nachweise

ORD-Eintrag
ord-11402d17cad94860b270b072a30f3c74
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132419B2

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