Sodium Hydroxide → HCID 86699006, compound

HRID 1520007Notes

Reaction equation

HRID 1520007 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][N:9]2[CH:13]=[C:12]([NH2:14])[CH:11]=[N:10]2)=[CH:3][CH:2]=1.N([O-])=O.[Na+].[N-:19]=[N+:20]=[N-].[Na+].[OH-].[Na+]>CC(O)=O.OS(O)(=O)=O.O>[N:14]([C:12]1[CH:11]=[N:10][N:9]([CH2:8][CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH:13]=1)=[N+:19]=[N-:20]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 608928391183808-98-1

Product 1

HCID 86699006HCID 86699006, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled solution (0° C.) of 1-(2-Pyridin-4-yl-ethyl)-1H-pyrazol-4-ylamine (300 mg; 2.66 mmol; 1.0 eq.) in AcOH (2.0 mL) and H2SO4 (1.0 mL) was added dropwise a solution of sodium nitrite (220 mg; 3.19 mmol; 1.2 eq.) in water (1.50 mL) and the reaction mixture was stirred at 0° C. for 1 hour. A solution of sodium azide (207 mg; 3.2 mmol; 1.2 eq.) in water (1.5 mL) was then added dropwise at 0° C. and the reaction mixture was stirred at 0° C. for 2 hours. The reaction mixture was then poured into ice water, basified to pH=10-11 with NaOH (5N) and extracted with EtOAc (twice). Combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated to afford the title compound as a dark oil, which was used without further purification in the next step. MS (ESI+): 215.0 (purity 98.7%).

Workup

  1. stirringthe reaction mixture was stirred at 0° C. for 2 hours
  2. extractionextracted with EtOAc (twice)
  3. washCombined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3d820194128f4642bbb0b92a2b231e22
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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