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Water → 3-Amino-6-chloro-4-methylpicolinic acid

HRID 887715
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HRID 887715 반응식
C(OC(=O)[NH:7][C:8]1[C:9]([C:16]#N)=[N:10][C:11]([Cl:15])=[CH:12][C:13]=1[CH3:14])(C)(C)C.[OH2:19].[OH-:20].[Na+]>S(=O)(=O)(O)O>[NH2:7][C:8]1[C:9]([C:16]([OH:20])=[O:19])=[N:10][C:11]([Cl:15])=[CH:12][C:13]=1[CH3:14]
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참가 물질

5

반응물 3

HCID 962Water2회HCID 14798Sodium HydroxideHCID 59355292(6-Chloro-2-cyano-4-methyl-pyridin-3-yl)-carbamic acid tert-butyl ester

생성물 1

HCID 593553013-Amino-6-chloro-4-methylpicolinic acid

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

반응 조건

온도
100 °C

실험 절차

(6-Chloro-2-cyano-4-methyl-pyridin-3-yl)-carbamic acid tert-butyl ester (3.72 g) was dissolved in concentrated sulfuric acid (19 mL) and stirred for 1 h at 100° C. The reaction mixture was cooled to room temperature and water (19 mL) was slowly added. The reaction mixture was warmed again to 100° C. and stirred at this temperature for 2 h. Water was added after cooling to room temperature, the mixture was cooled in an ice bath and the pH was adjusted to ˜14 by slow addition of solid sodium hydroxide. The aqueous solution was washed 2× with MTB-ether, the aqueous layer was then adjusted to pH ˜2 by addition of 5 M hydrochloric acid and extracted 3× with ethyl acetate. The combined organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuum to afford 2.25 g of the title compound of the formula

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. temperatureThe reaction mixture was warmed again to 100° C.
  3. stirringstirred at this temperature for 2 h
  4. temperatureafter cooling to room temperature
  5. temperaturethe mixture was cooled in an ice bath
  6. washThe aqueous solution was washed 2× with MTB-ether
  7. additionthe aqueous layer was then adjusted to pH ˜2 by addition of 5 M hydrochloric acid
  8. extractionextracted 3× with ethyl acetate
  9. washThe combined organic layer was washed with brine
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated in vacuum

출처 및 근거

ORD 기록
ord-e41ac4c2b7d74a53a3be901dac67fe09
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08247431B2

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