Hydrogen Bromide → 3-hydroxy-5-(2-methylphenethyl)pyridin-2(1H)-one

HRID 709080ノート

反応式

HRID 709080 の反応式
C[O:2][C:3]1[C:8]([O:9]C)=[CH:7][C:6]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[CH:5][N:4]=1.Br.O>CO.[Pd].C(O)(=O)C>[OH:9][C:8]1[C:3](=[O:2])[NH:4][CH:5]=[C:6]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH:7]=1

参加物

7

反応物 3

HCID 260Hydrogen BromideHCID 962WaterHCID 711862092,3-Dimethoxy-5-[(2-methylphenyl)ethynyl]pyridine2 回

生成物 1

HCID 711871703-hydroxy-5-(2-methylphenethyl)pyridin-2(1H)-one収率 18%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

反応条件

温度
180 °C

実験手順

2,3-Dimethoxy-5-[(2-methylphenyl)ethynyl]pyridine (Intermediate 33) (437 mg, 1.7 mmol) was hydrogenated in methanol using palladium on carbon as catalyst at 20 bar. The crude product was dissolved in acetic acid (5 ml) and 48% aqueous hydrobromic acid (5 ml) was added before the mixture was irradiated in the microwave with heating at 180° C. for 1 hour. The resulting mixture was then poured into water and the precipitated solid was filtered off and washed with water before being recrystallised from ethanol (twice) to afford 3-hydroxy-5-(2-methylphenethyl)pyridin-2(1H)-one (70 mg, 0.3 mmol, 18% yield).

後処理

  1. customwas irradiated in the microwave
  2. filtrationthe precipitated solid was filtered off
  3. washwashed with water
  4. custombefore being recrystallised from ethanol (twice)

出典と根拠

ORDレコード
ord-f9704ecec23d46a385f9603f77dcd32f
出典データセット
uspto-grants-2015_11
特許番号
US09180122B2

反応ノート

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