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

HRID 1187506

반응식

HRID 1187506 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

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.degree. 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. temperatureThe reaction mixture was heated in a sealed flask at 100.degree
  2. filtrationThe precipitate was collected by suction filtration
  3. washwashed with water and ether

출처 및 근거

ORD 기록
ord-1c57b5b7bae44642a79a4332b6b8f588
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673943B2

연결된 노트

불러오는 중…