Sulfamic Acid → 4-((5-Cyano-2-pyridinyl)oxy)benzoic acid

HRID 1177980Notes

Reaction equation

HRID 1177980 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=2)=[CH:5][CH:4]=1)=[O:2].S(=O)(=O)([OH:20])N.Cl([O-])=O.[Na+]>CC(C)=O.O.O>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([O:7][C:6]2[CH:16]=[CH:17][C:3]([C:1]([OH:20])=[O:2])=[CH:4][CH:5]=2)=[N:9][CH:10]=1)#[N:13]

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 471502166-(4-Formylphenoxy)nicotinonitrile

Product 1

HCID 521758604-((5-Cyano-2-pyridinyl)oxy)benzoic acidYield 86.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

6-(4-formyl-phenoxy)-nicotinonitrile (310 mg, 1.38 mmol) was dissolved in acetone-water mixture (3.5:3) (6.5 mL) and cooled to 0° C. Sulphamic acid (403 mg, 4.15 mmol) and sodium chlorite (499 mg, 5.52 mmol) dissolved in minimum amount of water were added and the resulting mixture was stirred at room temperature for half an hour. The reaction mixture was then diluted with water and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over sodium sulphate and concentrated to afford 288 mg 4-(5-cyano-pyridin-2-yloxy)-benzoic acid, (85.2% yield). LCMS Purity: 83.2%,

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a27e5bbf5e0d487487720818103440de
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

Loading…