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

HRID 603504ノート

反応式

HRID 603504 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 1197855,6-Dimethyl-2-pyridone収率 48.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
175 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-01411a0e5cce4fcc96e5371a953cf923
出典データセット
uspto-grants-2011_03
特許番号
US07906653B2

反応ノート

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