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

HRID 719178

Reaction equation

HRID 719178 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-11402d17cad94860b270b072a30f3c74
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Linked notes

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