Sodium Hydroxide → HCID 11823800, compound

HRID 719187Notes

Reaction equation

HRID 719187 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:18]2[C:9](=[N:10][C:11]3[C:16]([N:17]=2)=[C:15]2[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH3:24])[C:14]2=[CH:13][CH:12]=3)[CH:8]=[CH:7][C:6]=1F)=[O:4].[N-:26]=[N+]=[N-].[Na+].[OH-].[Na+]>CN(C)C=O.O>[CH3:1][O:2][C:3]([C:5]1[C:18]2[C:9](=[N:10][C:11]3[C:16]([N:17]=2)=[C:15]2[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH3:24])[C:14]2=[CH:13][CH:12]=3)[CH:8]=[CH:7][C:6]=1[NH2:26])=[O:4]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 10958632HCID 10958632, compound

Product 1

HCID 11823800HCID 11823800, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 10-fluoro-4-methoxy-benzo[a]phenazine-11-carboxylic acid methyl ester (IV.5) (466 mg) and sodium azide (900 mg) in N,N-dimethylformamide (10 mL) was heated at 90° C. for 18 hours. The reaction mixture was then cooled, diluted with water, and then sodium hydroxide solution was added resulting in a brown precipitate. This was collected by filtration and washed with water and ether to yield the desired title compound as a yellow solid (242 mg).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customresulting in a brown precipitate
  3. filtrationThis was collected by filtration
  4. washwashed with water and ether

Sources & evidence

ORD record
ord-b38638043cd141638db53ee96f7aea74
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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