Hydrochloric Acid → 2-Methylpyridine-4-carbonitrile

HRID 1497272ノート

反応式

HRID 1497272 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6].[CH3:10][Al](C)C.Cl>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:10][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 5686382-Chloro-4-cyanopyridineHCID 16682925Trimethylaluminum

生成物 1

HCID 119590732-Methylpyridine-4-carbonitrile収率 57.6%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 2-chloroisonicotinonitrile (2 g, 14.4 mmol), trimethylaluminum (7.94 ml, 15.9 mmol) and tetrakis(triphenylphosphine)palladium (0) (367 mg, 318 μmol) in dioxane (20.0 ml) was heated to reflux for 4 h. The reaction mixture was poured on 1N HCl and extracted two times with EtOAc. The aqueous layer was basified with 3N NaOH and extracted with EtOAc. The combined organic extracts were dried with Na2SO4 and evaporated. The remaining solid was purified by column chromatography (silica gel, dichloromethane/EtOAc 95:5) to afford the title compound (980 mg, 57%) as white solid. 1H NMR (CDCl3, 300 MHz): 2.64 (s, 3H), 7.34 (d, J=5.05 Hz 1H), 7.40 (s, 1H), 8.68 (d, J=5.05 Hz, 1H).

後処理

  1. temperatureto reflux for 4 h
  2. extractionextracted two times with EtOAc
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried with Na2SO4
  5. customevaporated
  6. customThe remaining solid was purified by column chromatography (silica gel, dichloromethane/EtOAc 95:5)

出典と根拠

ORDレコード
ord-9e76c94f427b412781233da037c20c9b
出典データセット
uspto-grants-2015_12
特許番号
US09199938B2

反応ノート

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