Sodium Azide → HCID 57708028, compound

HRID 1397695Notes

Reaction equation

HRID 1397695 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]([CH2:19]Cl)=[CH:7]2.[N-:21]=[N+]=[N-].[Na+]>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]([CH2:19][NH2:21])=[CH:7]2

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 57707975HCID 57707975, compound

Product 1

HCID 57708028HCID 57708028, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 8-chloro-3-(chloromethyl)-2-phenoxyquinoline (1 eq) in DMSO (0.25 M) was added NaN3 (3 eq) at rt and the mixture was stirred for 4 h at it. The mixture was diluted with water, extracted with EtOAc (2 times) and the combined organic layers were washed with water (2 times), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was dissolved in MeOH and treated with 10% Pd—C (5 wt %) and the mixture was then stirred under H2 balloon over night. The mixture was filtered through a Celite™ pad followed by removal of solvents to give (8-chloro-2-phenoxyquinolin-3-yl)methanamine.

Workup

  1. extractionextracted with EtOAc (2 times)
  2. washthe combined organic layers were washed with water (2 times)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in MeOH
  7. additiontreated with 10% Pd—C (5 wt %)
  8. stirringthe mixture was then stirred under H2 balloon over night
  9. filtrationThe mixture was filtered through a Celite™ pad
  10. customfollowed by removal of solvents

Sources & evidence

ORD record
ord-7a1dd552d290442b89fa7f752906f211
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

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