Ethanol → Ethyl 10-ethoxy-5-hydroxy-9-methoxycarbonylbenzo[alpha]-phenazine-6-carboxylate

HRID 1789074Notes

Reaction equation

HRID 1789074 reaction equation
O[C:2]1[C:11](=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:13])[C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[NH2:19][C:20]1[C:29]([NH2:30])=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]([O:31][CH2:32][CH3:33])[CH:21]=1.C(O)C>CN(C)C=O>[CH2:32]([O:31][C:22]1[C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:28][C:29]2[C:20]([CH:21]=1)=[N:19][C:11]1[C:2](=[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:4]([OH:13])=[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]3=1)[N:30]=2)[CH3:33]

Participants

5

Reactant 3

HCID 702EthanolHCID 13913221Methyl 4,5-diamino-2-ethoxybenzoateHCID 178470044HCID 178470044, compound

Product 1

HCID 137175504Ethyl 10-ethoxy-5-hydroxy-9-methoxycarbonylbenzo[alpha]-phenazine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 895 mg of ethyl 3-hydroxy-1,4-dihydro1,4-dioxo-2-naphthoate in 10 ml of N,N-dimethylformamide was added 620 mg of N,N'-carbonyldiimidazole, and the mixture was stirred at room temperature for 2 hours. To the mixture was added the crude methyl 4,5-diamino-2-ethoxybenzoate in 10 ml of N,N-dimethyl-formamide under ice cooling, and the mixture was stirred at room temperature overnight. To the reaction solution was added 200 ml of ethanol, and then the resulting precipitate was collected by filtration and recrystallized from chloroform - ethanol to give the title compound, m.p. 270°-273° C., yield of 531 mg.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. filtrationthe resulting precipitate was collected by filtration
  3. customrecrystallized from chloroform - ethanol

Sources & evidence

ORD record
ord-891c1c61ec8840a4be4dcb49b477b3d6
Source dataset
uspto-grants-1987_08
Patent number
US04686292

Reaction notes

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