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

HRID 709080노트

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HRID 709080 반응식
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

참가 물질

7

반응물 3

HCID 260Hydrogen BromideHCID 962WaterHCID 711862092,3-Dimethoxy-5-[(2-methylphenyl)ethynyl]pyridine2회

생성물 1

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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 176Acetic Acid용매HCID 887Methanol용매

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온도
180 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-f9704ecec23d46a385f9603f77dcd32f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09180122B2

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