Hydrochloric Acid → 2-Methylpyridine-4-carbonitrile

HRID 1497272노트

반응식

HRID 1497272 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

HCID 119590732-Methylpyridine-4-carbonitrile수율 57.6%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9e76c94f427b412781233da037c20c9b
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199938B2

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