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

HRID 1177980
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HRID 1177980 반응식
[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]
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 18366337
Propan-2-one--water (1/1)
용매

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온도
0 °C

실험 절차

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%,

후처리

  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

출처 및 근거

ORD 기록
ord-a27e5bbf5e0d487487720818103440de
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07842696B2

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