Carbon Dioxide → 3-hydroxy-6-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one

HRID 913042

반응식

HRID 913042 반응식
Cl.[OH:2][C:3]1[C:4](=[O:10])[CH:5]=[C:6]([CH3:9])[NH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)=O.[F:20][C:21]([F:27])([F:26])[CH:22](OC)[OH:23]>O.C(O)(=O)C>[OH:2][C:3]1[C:4](=[O:10])[CH:5]=[C:6]([CH3:9])[NH:7][C:8]=1[CH:22]([OH:23])[C:21]([F:27])([F:26])[F:20]

참가 물질

7

반응물 4

HCID 280Carbon DioxideHCID 98922,2,2-Trifluoro-1-methoxyethanolHCID 11430Potassium CarbonateHCID 672826585-hydroxy-2-methyl-1H-pyridin-4-one hydrochloride

생성물 1

HCID 250186523-hydroxy-6-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

5-Hydroxy-2-methyl-1H-pyridin-4-one hydrochloride (1.00 g, 6.19 mmol) and potassium carbonate (1.02 g, 7.42 mmol) was mixed together in water (10 mL) at room temperature, and stirred until evolution of carbon dioxide ceased. Then, 2,2,2-trifluoro-1-methoxy-ethanol (1.60 g, 12.4 mmol) was added. The reaction mixture was heated in a sealed flask at 100° C. for 20 h. The mixture was cooled down to RT and neutralized with acetic acid to pH at between 5 to 6. The precipitate was collected by suction filtration and washed with water and ether. Thus, 3-hydroxy-6-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one was obtained as an off-white solid (1.06 g, 76% yield). 1H NMR (90 MHz, DMSO-d6) δ (ppm): 6.09 (s, 1H, CH); 5.42 (apparent q, 1H, CH), 2.28 (s, 3H, CH3); MS-ESI (m/z) 224.1 [M+1]+, 206.1, 186.1, 178.1.

후처리

  1. filtrationThe precipitate was collected by suction filtration
  2. washwashed with water and ether

출처 및 근거

ORD 기록
ord-7b1e6d08f0f8468cbe07850641faef23
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026261B2

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