Hydrochloric Acid → 3-(2-Methoxybenzylamino)-2-phenylpyridine

HRID 1376817ノート

反応式

HRID 1376817 の反応式
[C:1]1([C:7]2[C:12]([NH2:13])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C([BH3-])#N.[Na+].[CH3:19][O:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=O>CO>[CH3:19][O:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][NH:13][C:12]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][CH:9]=[CH:10][CH:11]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 86582-MethoxybenzaldehydeHCID 27627843-Amino-2-phenylpyridineHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 152327123-(2-Methoxybenzylamino)-2-phenylpyridine収率 56.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

Under a nitrogen atmosphere, in a round-bottom flask were placed 500 mg (2.9 mmol) of 2-phenyl-3-aminopyridine, 10 mL of methanol and 1 g of 3A molecular sieves. The pH of the system was adjusted to ca. 4.5, using methanol saturated with HCl, and 190 mg (2.9 mmol) of sodium cyanoborohydride was added to the system. The pH of the system was adjusted to 4.5, 474 mg (3.5 mmol) of 2-methoxybenzaldehyde was added and the mixture was stirred at room temperature overnight. The mixture was filtered through (Celite®) and the filtrate was concentrated. The residue was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate, the layers were separated and the aqueous phase was extracted with three portions of CH2Cl2. The combined organic fractions were dried (Na2SO4) and concentrated with a rotary evaporator. The crude material was purified by flash column chromatography to obtain 475 mg of 3-(2-methoxybenzylamino)-2-phenylpyridine. Mp. 128°-129° C.

後処理

  1. customUnder a nitrogen atmosphere, in a round-bottom flask were placed
  2. additionwas added to the system
  3. additionwas added
  4. filtrationThe mixture was filtered through (Celite®)
  5. concentrationthe filtrate was concentrated
  6. customThe residue was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate
  7. customthe layers were separated
  8. extractionthe aqueous phase was extracted with three portions of CH2Cl2
  9. dry with materialThe combined organic fractions were dried (Na2SO4)
  10. concentrationconcentrated with a rotary evaporator
  11. customThe crude material was purified by flash column chromatography

出典と根拠

ORDレコード
ord-52084417492c4f45b172a5786b3d42fb
出典データセット
uspto-grants-1997_09
特許番号
US05663349

反応ノート

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