3-Phenylpyridine → 5-Phenyl-2-pyridinamine

HRID 489135ノート

反応式

HRID 489135 の反応式
[C:1]1([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2-:13].[Na+]>C1(C)C=CC(C)=CC=1>[NH2:13][C:8]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:12][CH:11]=[CH:10][N:9]=1.[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][N:9]=1

参加物

5

反応物 2

HCID 138863-PhenylpyridineHCID 24533Sodium amide

生成物 2

HCID 1050975-Phenyl-2-pyridinamine収率 55.8%HCID 27627953-Phenylpyridin-2-amine

試薬・触媒・溶媒 1

HCID 7809P-Xylene溶媒

実験手順

2-amino-3-phenyl pyridine was prepared as follows: 3-phenyl pyridine (300 mg, 2 mmol) was dissolved in para-xylene (6 ml), and sodamide (84 mg, 2.1 mmol) was then added. The reaction mixture was heated to reflux temperature for 8 hours. The reaction mixture was cooled, poured onto ice/water (25 ml), and extracted with dichloromethane. The organic extracts were washed with water and brine, and dried over anhydrous sodium sulphate. The sodium sulphate was removed by filtration, and the filtrate was evaporated to dryness and recrystallized from a mixture of diethyl ether and petroleum ether to provide 2-amino-5-phenyl pyridine (95 mg). The mother liquors from the crystallization were evaporated to dryness and subjected to purification by column chromatography (silica), thereby eluting the solvent ethyl acetate:petroleum ether (30:70). The desired product, 2-amino-3-phenyl pyridine, was obtained as a fine yellow powder (15 mg).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature for 8 hours
  3. temperatureThe reaction mixture was cooled
  4. additionpoured onto ice/water (25 ml)
  5. extractionextracted with dichloromethane
  6. washThe organic extracts were washed with water and brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customThe sodium sulphate was removed by filtration
  9. customthe filtrate was evaporated to dryness
  10. customrecrystallized from a mixture of diethyl ether and petroleum ether

出典と根拠

ORDレコード
ord-021f73f6743b4b9bafbd63144bd27a87
出典データセット
uspto-grants-2005_12
特許番号
US06977255B2

反応ノート

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