Sulfuric Acid → 5-Iodo-1H-indazole-3-carboxylic acid

HRID 1454929노트

반응식

HRID 1454929 반응식
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[OH-:13].[Na+].[N:15]([O-])=O.[Na+].S(=O)(=O)(O)O.[Sn](Cl)(Cl)(Cl)Cl>O>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:15]=[C:5]2[C:6]([OH:11])=[O:13]

참가 물질

7

반응물 5

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 886955-IodoisatinHCID 23668193Sodium Nitrite

생성물 1

HCID 218135505-Iodo-1H-indazole-3-carboxylic acid

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

5-Iodoisatin (5 g, 18.3 mmol) is heated in the presence of sodium hydroxide (0.77 g, 19.2 mmol in 12 ml H2O) until dissolution is obtained and then the reaction mixture is cooled to 0° C. A sodium nitrite solution cooled beforehand to 0° C. (1.26 g, 18.3 mmol in 5.5 ml H2O) is added. The paste obtained is added in small portions, with vigorous stirring, to a sulphuric acid solution (3.40 g, 34.8 mmol in 37 ml H2O) precooled to 0° C. so that the temperature does not exceed 4° C. The stirring is maintained for 15 min and then a tin chloride solution (SnCl2.2H2O, 9.91 g, 43.9 mmol in 15 ml concentrated HCl) is slowly added such that the temperature does not exceed 4° C. The medium is allowed to react for several hours. The reaction mixture is filtered. The solid is washed with boiling water and then taken up in ethanol in the hot state. The insoluble impurities are removed by filtration.

후처리

  1. customis obtained
  2. custombeforehand to 0° C.
  3. additionis added
  4. customThe paste obtained
  5. customprecooled to 0° C. so that the temperature
  6. customdoes not exceed 4° C
  7. temperatureThe stirring is maintained for 15 min
  8. customdoes not exceed 4° C
  9. customto react for several hours
  10. filtrationThe reaction mixture is filtered
  11. washThe solid is washed with boiling water
  12. customThe insoluble impurities are removed by filtration

출처 및 근거

ORD 기록
ord-c09e2439d5834a6ca9dda9d72771dd5b
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482342B2

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