Dimethylformamide dimethyl acetal → 4-(4-Methoxypyridin-2-yl)-2-nitrobenzaldehyde

HRID 1060003노트

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HRID 1060003 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)[CH:4]=1.C[O:20]C(OC)N(C)C>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[O:20])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)[CH:4]=1

참가 물질

4

반응물 2

HCID 78373Dimethylformamide dimethyl acetalHCID 186310034-(4-Methoxypyridin-2-yl)-2-nitrotoluene

생성물 1

HCID 186675454-(4-Methoxypyridin-2-yl)-2-nitrobenzaldehyde

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
140 °C

실험 절차

To a solution of 4-(4-methoxypyridin-2-yl)-2-nitrotoluene (2.5 g) in N,N-dimethylformamide (15 ml) was added N,N-dimethylformamide dimethyl acetal (2.72 ml), and the mixture was stirred at 140° C. for 24 hours under a nitrogen atmosphere. The reaction mixture was evaporated under reduced pressure, and the residue was suspended in tetrahydrofuran (60 ml) and water (60 ml). Sodium metaperiodate (6.57 g) was added to the suspension, and the mixture was stirred at ambient temperature for 3 hours. The reaction mixture was filtered, and the filtrate was extracted with ethyl acetate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 150 g, 25-45% ethyl acetate in n-hexane) to give 4-(4-methoxypyridin-2-yl)-2-nitrobenzaldehyde (1.99 g).

후처리

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additionSodium metaperiodate (6.57 g) was added to the suspension
  3. stirringthe mixture was stirred at ambient temperature for 3 hours
  4. filtrationThe reaction mixture was filtered
  5. extractionthe filtrate was extracted with ethyl acetate
  6. washThe separated organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography (silica gel 150 g, 25-45% ethyl acetate in n-hexane)

출처 및 근거

ORD 기록
ord-f5c2a905307645d496bfa72357bead6e
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521643B1

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