Water → HCID 67485692, compound

HRID 1809604Notes

Reaction equation

HRID 1809604 reaction equation
[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:17]N1C(=O)CCC1=O.O>CN(C=O)C>[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)=[CH:6][C:5]([Cl:17])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 66994464HCID 66994464, compound

Product 1

HCID 67485692HCID 67485692, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(2-aminopyridin-3-yloxy)benzonitrile (5.6 g, 26.5 mmol) in DMF (100 mL) was added N-chlorosuccinimide (4.25 g, 31.8 mmol) and stirred at 80° C. for 14 h. The reaction mixture was cooled to ambient temperature and poured into water (100 mL). The aqueous suspension was extracted with EtOAc and the combined organic layers were washed with water. The organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified on silica gel (20% EtOAc/hexanes) and triturated with methanol to afford 4-(2-amino-5-chloropyridin-3-yloxy)benzonitrile (2.75 g, 42.2% yield) as a bright yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionThe aqueous suspension was extracted with EtOAc
  3. washthe combined organic layers were washed with water
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica gel (20% EtOAc/hexanes)
  8. customtriturated with methanol

Sources & evidence

ORD record
ord-a5cfd2b7963e49ff84b59f5660c79c9e
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

Loading…