Hydrochloric Acid → N-(4-Formyl-pyridin-3-yl)-2,2-dimethyl-propionamide

HRID 605004

반응식

HRID 605004 반응식
[CH3:1][C:2]([CH3:13])([CH3:12])[C:3]([NH:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:4].C([Li])CCC.CCCCCC.CN(C)[CH:27]=[O:28].Cl>O1CCCC1>[CH:27]([C:11]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[NH:5][C:3](=[O:4])[C:2]([CH3:13])([CH3:12])[CH3:1])=[O:28]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 46550442,2-dimethyl-N-(pyridin-3-yl)propanamideHCID 178418244HCID 178418244, 화합물

생성물 1

HCID 1519484N-(4-Formyl-pyridin-3-yl)-2,2-dimethyl-propionamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-70 °C

실험 절차

A solution of 2,2-dimethyl-N-(3-pyridinyl)propanamide (3.56 gm, 20 mmol) (prepared as described in J. Org. Chem. 48, 3401 (1983)) in anhydrous tetrahydrofuran (40 mL) was cooled to −70° C. and a solution of 2.5 M n-butyl lithium/hexane (20 mL, 50 mmol) was added dropwise maintaining the temperature at −70° C. This reaction was slowly warmed to −5° C. giving a copious precipitate. This mixture was cooled to −70° C. and dry dimethyl formamide (4.64 mL, 60 mmol) was added. The reaction was allowed to warm to room temperature giving a clear yellow solution. This reaction was poured into 8 N aqueous HCl (16 mL) and ice. After stirring for 10 minutes the pH of the solution was adjusted to 7 and extracted with diethyl ether. The organic layer was dried (Na2SO4), filtered and the solvent evaporated. The residue was purified by column chromatography eluting with 30-100% ethyl acetate/hexane. The appropriate fractions were combined and the solvent removed in vacuo to give the title compound as a solid. 1H-NMR (500 MHz, CDCl3): δ 10.92 (1H, br s), 10.15 (1H, s), 10.05 (1H, s), 8.62 (2H, d, J=4.9 Hz), 7.56 (1H, d, J=4.9 Hz),), 1.39 (9H, s). m/e (m+1): 235.3.

후처리

  1. temperatureThis reaction was slowly warmed to −5° C.
  2. customgiving a copious precipitate
  3. temperatureThis mixture was cooled to −70° C.
  4. temperatureto warm to room temperature
  5. customgiving a clear yellow solution
  6. extractionextracted with diethyl ether
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. customThe residue was purified by column chromatography
  11. washeluting with 30-100% ethyl acetate/hexane
  12. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-5ea91fc4321245949cd986a6908d3b2d
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910561B2

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