Sodium Azide → HCID 117601487, compound

HRID 1773676Notes

Reaction equation

HRID 1773676 reaction equation
[Br:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:13])[NH:7]2.[N-]=[N+]=[N-].[Na+].[C:18]([O-])(O)=O.[Na+]>CS(O)(=O)=O>[Br:1][C:2]1[C:3]2[CH2:18][CH2:4][CH2:5][C:6](=[O:13])[NH:7][C:8]=2[CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 117601883HCID 117601883, compound

Product 1

HCID 117601487HCID 117601487, compound

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

5-Bromo-6-methyl-3,4-dihydroquinolin-2(1H)-one (477.7 mg, 1.998 mmol) was treated with NaN3 (194.8 mg, 0.938 mmol, 1.5 equiv) in MeSO3H (3 g) at 0° C. to room temperature for 1 h. The mixture was neutralized with NaHCO3 and extracted with EtOAc (30 mL×3). The organic layer was washed with brine (30 mL) and dried over Na2SO4. The solvent was removed under a reduced pressure and the crude product was recrystallized from EtOAc (10 mL) to give 6-bromo-7-methyl-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one.

Workup

  1. extractionextracted with EtOAc (30 mL×3)
  2. washThe organic layer was washed with brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under a reduced pressure
  5. customthe crude product was recrystallized from EtOAc (10 mL)

Sources & evidence

ORD record
ord-7e1a86cfc93447e7beb31ca49fe27cb7
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

Loading…