Iodine → 5-Iodo-2-methylpyridin-4-amine

HRID 400572

반응식

HRID 400572 반응식
[I:1]I.[CH3:3][C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][N:5]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>O>[NH2:10][C:8]1[CH:9]=[C:4]([CH3:3])[N:5]=[CH:6][C:7]=1[I:1].[NH2:10][C:8]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:3])[C:9]=1[I:1]

참가 물질

7

반응물 4

HCID 807IodineHCID 8857Ethyl Acetate3회HCID 10340Sodium CarbonateHCID 7286704-Amino-2-methylpyridine

생성물 2

HCID 534400975-Iodo-2-methylpyridin-4-amine수율 11%HCID 534852533-Iodo-2-methylpyridin-4-amine수율 5%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

A solution of KI (1.96 g, 11.9 mmol) and I2 (1.87 g, 7.36 mmol) in 10 mL of water was added to a refluxing solution of the 2-methylpyridin-4-ylamine (1.00 g, 9.25 mmol) and sodium carbonate (683 mg, 6.44 mmol) in 5 mL of water. The mixture was heated at reflux for 2 hours, cooled to room temperature, and treated with 20 mL of ethyl acetate (EtOAc). Phases were separated and the aqueous layer was extracted with three 20 mL portions of ethyl acetate. The combined organic layers were washed with a saturated aqueous sodium thiosulfate (Na2S2O3) solution, dried over magnesium sulfate, and concentrated in vacuo. Flash chromatography (30% ethyl acetate in hexanes to 100% ethyl acetate, gradient) of the resulting residue yielded 4-amino-3-iodo-6-methylpyridine (first eluting: 226 mg, 11% yield) and 4-amino-3-iodo-2-methylpyridine (second eluting: 116 mg; 5% yield).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customPhases were separated
  4. extractionthe aqueous layer was extracted with three 20 mL portions of ethyl acetate
  5. washThe combined organic layers were washed with a saturated aqueous sodium thiosulfate (Na2S2O3) solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1849fb6f36114f8fb9bcbb9b71dc9f02
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741897B2

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