Sulfuric Acid → Ethyl 3-hydroxyisonicotinate

HRID 2109051

반응식

HRID 2109051 반응식
N[C:2]1[CH:12]=[N:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].S(=O)(=O)(O)[OH:14].N([O-])=O.[Na+].C(=O)([O-])O.[Na+]>O>[OH:14][C:2]1[CH:12]=[N:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 2736365Ethyl 3-AminoisonicotinateHCID 23668193Sodium Nitrite

생성물 1

HCID 12326192Ethyl 3-hydroxyisonicotinate

시약·촉매·용매 1

HCID 962Water용매3회

실험 절차

Ethyl 3-aminoisonicotinate (5.55 g) is suspended in water (70 ml), and thereto added conc. sulfuric acid (4.0 ml). The reaction solution is cooled with ice, and a solution of sodium nitrite (2.79 g) in water (30 ml) is added dropwise thereto. The reaction solution is stirred under the same cooling conditions for 20 minutes and then at 90° C. for 80 minutes. The reaction solution is diluted with water (100 ml) and the solution is adjusted to pH 8 to 9 by addition of saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform. The organic layer is dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1) to give ethyl 3-hydroxyisonicotinate (2.64 g).

후처리

  1. temperatureThe reaction solution is cooled with ice
  2. temperaturesame cooling conditions for 20 minutes
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-b3701f335155479b93e5a93e0afe6245
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514449B2

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