Diazomethane → HCID 131713690, compound

HRID 2418478Notes

Reaction equation

HRID 2418478 reaction equation
[OH:1][C:2]1[C:15]([CH2:16][C:17]([NH:19][CH2:20][CH2:21][Cl:22])=[O:18])=[C:14]2[C:5]([N:6]=[C:7]3[C:12](=[N:13]2)[CH:11]=[CH:10][CH:9]=[CH:8]3)=[C:4]2[CH:23]=[CH:24][CH:25]=[CH:26][C:3]=12.[N+](=[CH2:29])=[N-]>C(O)C>[CH3:29][O:1][C:2]1[C:15]([CH2:16][C:17]([NH:19][CH2:20][CH2:21][Cl:22])=[O:18])=[C:14]2[C:5]([N:6]=[C:7]3[C:12](=[N:13]2)[CH:11]=[CH:10][CH:9]=[CH:8]3)=[C:4]2[CH:23]=[CH:24][CH:25]=[CH:26][C:3]=12

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 137175481HCID 137175481, compound

Product 1

HCID 131713690HCID 131713690, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 100 of 5-hydroxy-N-β-chloroethylbenzo[a]phenazine-6-carboxyamide in 10 ml of ethanol was added an excess amount of diazomethane ethereal solution, followed by stirring at room temperature overnight. The solvent was concentrated under reduced pressure, and the resulting solid was recrystallized from acetic acid to give 103 mg (99% yield) of 5-methoxy-N-β-chloroethylbenzo[a]-phenazine-6-carboxyamide as yellow needles, m.p. 211°-213° C., Anal. Calcd. (%) for C20H16N3O2Cl; C, 65.89; H, 4.29; N, 11.28; Found: C, 65.67; H, 4.41; N, 11.49

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. customthe resulting solid was recrystallized from acetic acid

Sources & evidence

ORD record
ord-b157771422d7417183a4f44519c0f6ad
Source dataset
uspto-grants-1984_09
Patent number
US04472578

Reaction notes

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