Hydrochloric Acid → 5,6-Dimethyl-2-pyridone

HRID 603504노트

반응식

HRID 603504 반응식
[CH3:1][C:2]1[CH:3]=[C:4](C#N)[C:5](=[O:9])[NH:6][C:7]=1[CH3:8].Cl.[OH-].[Na+]>O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5](=[O:9])[NH:6][C:7]=1[CH3:8]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5905325,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

생성물 1

HCID 1197855,6-Dimethyl-2-pyridone수율 48.4%

시약·촉매·용매 1

HCID 962Water용매2회

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온도
175 °C

실험 절차

A 100 mL Parr reactor was charged with 5,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile (Example 475, 3.00 g, 20.3 mmol), concentrated hydrochloric acid (18 mL), and water (18 mL). The reactor was slowly heated to 175° C. for 9 h and then cooled to rt. The solution was basified with 1N NaOH in water and was extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered, and concentrated in vacuo, yielding the title compound (1.21 g, 48%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.36 (bs, 1H), 7.18 (d, 1H), 6.04 (d, 1H), 2.10 (s, 3H), 1.93 (s, 3H).

후처리

  1. temperaturecooled to rt
  2. extractionwas extracted with EtOAc
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-01411a0e5cce4fcc96e5371a953cf923
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906653B2

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