Benzyl Bromide → 4-Benzyloxy-benzo[a]phenazine-11-carboxylic Acid

HRID 719177Notes

Reaction equation

HRID 719177 reaction equation
[OH:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]3[C:19]([N:18]=[C:17]4[C:12]([CH:13]=[CH:14][CH:15]=[C:16]4[C:20]([OH:22])=[O:21])=[N:11]3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)C.C(OCC)(=O)C>[CH2:25]([O:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]3[C:19]([N:18]=[C:17]4[C:12]([CH:13]=[CH:14][CH:15]=[C:16]4[C:20]([OH:22])=[O:21])=[N:11]3)=[C:6]2[CH:5]=[CH:4][CH:3]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 178524229HCID 178524229, compound

Product 1

HCID 109049944-Benzyloxy-benzo[a]phenazine-11-carboxylic Acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-hydroxy-benzo[a]phenazine-11-carboxylic acid (80 mg), sodium hydroxide (34 mg) and benzyl bromide (100 μL) in ethanol (2 mL) was heated to reflux for 4 hours. The reaction mixture was then cooled, diluted with ethyl acetate, washed with dilute acid, dried (MgSO4) and the solvent removed in vacuo to yield the crude title compound as a brown solid (50 mg).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. temperatureThe reaction mixture was then cooled
  4. washwashed
  5. additionwith dilute acid
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-3d7257bc9e1a4665b38c6815a9e7bf34
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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