O-Phenylenediamine → 86266-79-7

HRID 2418472Notes

Reaction equation

HRID 2418472 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=O)[C:4](OC)=[C:3]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[C:20]1([NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH2:26]>C(O)C>[OH:1][C:2]1[C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:4]2[C:5]([N:26]=[C:21]3[C:20](=[N:27]2)[CH:25]=[CH:24][CH:23]=[CH:22]3)=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=12

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 13112774HCID 13112774, compound

Product 1

HCID 13599770186266-79-7Yield 93.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.63 g of ethyl 1,4-dihydro-1,4-dioxo-3-methoxy-2-naphthoate and 1.3 g of o-phenylenediamine in 50 ml of ethanol was heated at reflux for an hour. After cooling, the precipitated solid was collected by filtration and recrystallized from ethanol to give 2.972 g (93.5% yield) of ethyl 5-hydroxybenzo[a]phenazine-6-carboxylate as yellow needles, m.p. 126°-127° C., Anal. CAlcd. (%) for C19H14N2O3 : C, 71.69; H, 4.43; N, 8.80; Found: C, 71.81; H, 4.21; N, 8.90

Workup

  1. temperaturewas heated
  2. temperatureat reflux for an hour
  3. temperatureAfter cooling
  4. filtrationthe precipitated solid was collected by filtration
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a54b30bb12da49a6ae5eec01276ba61c
Source dataset
uspto-grants-1984_09
Patent number
US04472578

Reaction notes

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