Acetic Acid → 4-Methyl-2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine

HRID 77898

반응식

HRID 77898 반응식
C(O)(=O)C.[CH3:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([O:12][CH2:13][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=2)[CH:7]=1.[N+:22]([CH3:25])([O-:24])=[O:23].C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.O>[CH3:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([O:12][CH2:13][C:14]2[CH:21]=[CH:20][C:17](/[CH:18]=[CH:25]/[N+:22]([O-:24])=[O:23])=[CH:16][CH:15]=2)[CH:7]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 592554674-(4-Methyl-pyridin-2-yloxymethyl)-benzaldehyde

생성물 1

HCID 592551344-Methyl-2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine수율 109.4%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To an acetic acid (20.0 mL) solution of 4-(4-methyl-pyridin-2-yloxymethyl)-benzaldehyde (2.60 g, 11.5 mmol) described in Manufacturing Example 43-1-2 were added nitromethane (3.50 g, 57.3 mmol) and ammonium acetate (1.76 g, 22.9 mmol) at room temperature under nitrogen atmosphere, which was stirred for 4 hours at 100° C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (3.40 g) as a crude product.

후처리

  1. extractionthe organic layer was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure

출처 및 근거

ORD 기록
ord-cc6dd927238f4dbab11b01f4a7bf78c3
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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