Sodium Nitrite → HCID 178428607, compound

HRID 505565Notes

Reaction equation

HRID 505565 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([Cl:17])[CH:16]=1)[O:5][C:6]1[C:7](N)=[N:8][CH:9]=[CH:10][C:11]=1[CH3:12].N([O-])=[O:19].[Na+]>OS(O)(=O)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([Cl:17])[CH:16]=1)[O:5][C:6]1[C:7]([OH:19])=[N:8][CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

5

Reactant 2

HCID 23668193Sodium Nitrite2×HCID 684265783-(3-Bromo-5-chlorophenoxy)-4-methylpyridin-2-amine

Product 1

HCID 178428607HCID 178428607, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
100 °C

Procedure

To an ice cooled suspension of 3-(3-bromo-5-chlorophenoxy)-4-methylpyridin-2-amine (600 mg, 1.913 mmol) in 5% aqueous H2SO4 (10 mL) was added a solution of sodium nitrite (198 mg, 2.87 mmol) in water (1 mL). The suspension was stirred in an ice bath for 30 minutes, after which it was added to a solution of 5% aqueous H2SO4 (10 mL), and the mixture was warmed to 100° C. and maintained at 100° C. for 1.5 hours. After this time, the mixture was cooled to 0° C. and treated with additional sodium nitrite (60 mg, 0.86 mmol) and then heated at 100° C. for 20 minutes. After this time, the mixture was cooled to 25° C., the resulting solid was collected by filtration, washed with water (10 mL), and dried under high vacuum to give the title compound. HRMS (M+1)=313.9577.

Workup

  1. temperaturemaintained at 100° C. for 1.5 hours
  2. temperatureAfter this time, the mixture was cooled to 0° C.
  3. temperatureheated at 100° C. for 20 minutes
  4. temperatureAfter this time, the mixture was cooled to 25° C.
  5. filtrationthe resulting solid was collected by filtration
  6. washwashed with water (10 mL)
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-b727e843bfdd41e3a147eb3d1f5a7a44
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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