Diazomethane → HCID 13074543, compound

HRID 2418474Notes

Reaction equation

HRID 2418474 reaction equation
[N+](=[CH2:3])=[N-].[OH:4][C:5]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:17]2[C:8]([N:9]=[C:10]3[C:15](=[N:16]2)[CH:14]=[CH:13][CH:12]=[CH:11]3)=[C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=12>CO>[CH3:3][O:4][C:5]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:17]2[C:8]([N:9]=[C:10]3[C:15](=[N:16]2)[CH:14]=[CH:13][CH:12]=[CH:11]3)=[C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=12

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 13599770186266-79-7

Product 1

HCID 13074543HCID 13074543, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An excess amount of diazomethane ethereal solution was added to a suspension of 640 mg of ethyl 5-hydroxybenzo[a]-phenazine-6-carboxylate in 8 ml of methanol and the mixture was left to stand overnight. The solvent was evaporated off under reduced pressure and the residual powder was recrystallized from ethanol to give 626 mg (91.5% yield) of ethyl 5-methoxybenzo[a]phenazine-6-carboxylate as orange prisms, m.p. 155°-157° C., Anal. Calcd. (%) for C20H16N2O3 : C, 72.28; H, 4.85; N, 8.43; Found: C, 72.41; H, 4.66; N, 8.18

Workup

  1. waitthe mixture was left
  2. customThe solvent was evaporated off under reduced pressure
  3. customthe residual powder was recrystallized from ethanol

Sources & evidence

ORD record
ord-612bc8d44e3c45bd861b98171f3364a7
Source dataset
uspto-grants-1984_09
Patent number
US04472578

Reaction notes

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