Water → HCID 178440698, compound

HRID 1953466Notes

Reaction equation

HRID 1953466 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[C:9]([C:16]#[N:17])=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].[N-:20]=[N+:21]=[N-:22].[Na+].O>CN(C=O)C>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[C:9]([C:16]1[NH:22][N:21]=[N:20][N:17]=1)=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 23296261HCID 23296261, compound

Product 1

HCID 178440698HCID 178440698, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

6-tert-Butyl-3-cyano-1,2-dihydroquinolin-2-one (1.74 g, 7.7 mmol) was dissolved in DMF (20 ml), and ammonium chloride (1.65 g, 30.8 mol) and sodium azide (2.00 g, 30.8 mol) were added to the resultant mixture. The mixture was stirred at a bath temperature of 120° C. for 16 hours. Water added to the reaction mixture. After removal of the precipitates by filtration, the reaction mixture was recrystallized from DMF-methanol. The crystals that precipitated were collected, to thereby obtain the title compound as yellow powder (1.08 g, 4.0 mmol, 52%).

Workup

  1. customAfter removal of the
  2. customprecipitates by filtration
  3. customthe reaction mixture was recrystallized from DMF-methanol
  4. customThe crystals that precipitated
  5. customwere collected

Sources & evidence

ORD record
ord-5ea5a9cb5a3d449992879efb089dcb5f
Source dataset
uspto-grants-2000_09
Patent number
US06117886

Reaction notes

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