Methanol → HCID 51357512, compound

HRID 1623767Notes

Reaction equation

HRID 1623767 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:17])=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:8].[OH-].[K+].CO.[K].Br[CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:25]>O.CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH3:25])=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:8]

Participants

8

Reactant 5

HCID 887MethanolHCID 11454(1-Bromoethyl)benzeneHCID 14797Potassium HydroxideHCID 5462222PotassiumHCID 24285249HCID 24285249, compound

Product 1

HCID 51357512HCID 51357512, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The compound 5-bromo-2-hydroxy-N-3-pyridinylbenzamide (may be prepared as described in Description 35; 300 mg, 1.02 mmol) was added to a solution of potassium hydroxide (57.4 mg, 1.02 mmol) in methanol (2 ml, 49.4 mmol). The mixture was then stirred at room temperature for 15 min and the solvent was removed in vacuo. To the potassium salt was added DMF (10 ml) and (1-bromoethyl)benzene (189 mg, 1.023 mmol), The reaction mixture was then heated under reflux for 2 h. The mixture was cooled, diluted with water (20 ml) and the precipitate was collected, and finally crystallized from ethyl acetate to yield the title compound. 63 mg.

Workup

  1. customthe solvent was removed in vacuo
  2. temperatureThe reaction mixture was then heated
  3. temperatureunder reflux for 2 h
  4. temperatureThe mixture was cooled
  5. customthe precipitate was collected
  6. customfinally crystallized from ethyl acetate

Sources & evidence

ORD record
ord-38a8cf9f64744a70adea8a733c8a9124
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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