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

HRID 400572

反応式

HRID 400572 の反応式
[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]

参加物

7

反応物 4

HCID 807IodineHCID 8857Ethyl Acetate3 回HCID 10340Sodium CarbonateHCID 7286704-Amino-2-methylpyridine

生成物 2

HCID 534400975-Iodo-2-methylpyridin-4-amine収率 11%HCID 534852533-Iodo-2-methylpyridin-4-amine収率 5%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1849fb6f36114f8fb9bcbb9b71dc9f02
出典データセット
uspto-grants-2014_06
特許番号
US08741897B2

関連ノート

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