Sodium Nitrite → HCID 178509954, compound

HRID 1952383Notes

Reaction equation

HRID 1952383 reaction equation
N[C:2]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([Cl:17])[CH:16]=2)[C:12]#[N:13])=[C:6]([Cl:18])[CH:5]=[CH:4][N:3]=1.N([O-])=[O:20].[Na+]>OS(O)(=O)=O>[Cl:17][C:15]1[CH:14]=[C:11]([CH:10]=[C:9]([O:8][C:7]2[C:2]([OH:20])=[N:3][CH:4]=[CH:5][C:6]=2[Cl:18])[CH:16]=1)[C:12]#[N:13]

Participants

4

Reactant 2

HCID 23668193Sodium Nitrite2×HCID 59529739HCID 59529739, compound

Product 1

HCID 178509954HCID 178509954, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 3-[(2-amino-4-chloropyridin-3-yl)oxy]-5-chlorobenzonitrile (590 mg, 2.106 mmol) in 5% aqueous H2SO4 (20 mL) cooled over an ice bath for 5 minutes was added sodium nitrite (247 mg, 3.58 mmol) and stirred 5 minutes. This mixture was then heated to 100° C. for 5 minutes. The mixture was re-cooled over an ice bath and treated with additional sodium nitrite (124 mg, 1.79 mmol), stirred cold for another 5 minutes and then heated to 100° C. for 5 minutes. The reaction mixture was again cooled over an ice bath and the resulting white solid was filtered and washed with water (4×5 mL). This solid was dried under high vacuum to provide the title compound. LRMS (M+1): 280.7.

Workup

  1. temperaturecooled over an ice bath for 5 minutes
  2. temperatureThe mixture was re-cooled over an ice bath
  3. stirringstirred cold for another 5 minutes
  4. temperatureheated to 100° C. for 5 minutes
  5. temperatureThe reaction mixture was again cooled over an ice bath
  6. filtrationthe resulting white solid was filtered
  7. washwashed with water (4×5 mL)
  8. customThis solid was dried under high vacuum

Sources & evidence

ORD record
ord-0d918986f3e64c9c838a3a3fe73092c3
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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