Hydrochloric Acid → 4-Methoxy-benzo[a]phenazine-11-carboxylic Acid

HRID 719162Notes

Reaction equation

HRID 719162 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](=O)[C:8]2=O.COC1C=CC=C2C=1CCCC2=O.[Se](=O)=O.C(O)(=O)C.C(O)(=O)C.[NH2:39][C:40]1[C:48]([NH2:49])=[CH:47][CH:46]=[CH:45][C:41]=1[C:42]([OH:44])=[O:43].Cl>C(O)C>[CH3:1][O:2][C:3]1[C:4]2=[CH:5][CH:6]=[C:7]3[C:8]([N:39]=[C:40]4[C:48]([CH:47]=[CH:46][CH:45]=[C:41]4[C:42]([OH:44])=[O:43])=[N:49]3)=[C:9]2[CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24007Selenium DioxideHCID 366205-MethoxytetraloneHCID 123364105-Methoxynaphthalene-1,2-dioneHCID 857879142,3-Diamino-benzoic acid, diacetate salt

Product 1

HCID 111202464-Methoxy-benzo[a]phenazine-11-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-methoxy-[1,2]naphthoquinone (prepared by treatment of 5-methoxytetralone with selenium dioxide, A. Bekaert et al Tetrahedron Letters 38, 24, 4219–4220, 1997) (1.98 g), 2,3-diamino-benzoic acid, diacetate salt, (J. Chem. Soc. Perkin. Trans I, 1984, p2019) (4.03 g) and conc. hydrochloric acid (2.2 mL) was heated to reflux in ethanol (20 mL) for 4 hours. The reaction mixture was cooled and the precipitate collected by filtration, and washed with ethanol and ether to yield the title compound as a beige solid (2.74 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe precipitate collected by filtration
  3. washwashed with ethanol and ether

Sources & evidence

ORD record
ord-5c818a20cc6446c287925c525c16d57a
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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