Sulfuric Acid → 6-Chloropyridine-3-carbaldehyde

HRID 130900

반응식

HRID 130900 반응식
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[CH:4][N:3]=1.C1(C)C=CC=CC=1.CC(C[AlH]CC(C)C)C.[OH:26]S(O)(=O)=O>CO>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH:6]=[O:26])=[CH:8][CH:9]=1

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 51520946-Chloro-3-pyridinecarbonitrile

생성물 1

HCID 27640536-Chloropyridine-3-carbaldehyde수율 62%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

Combine 6-chloro-nicotino-nitrile (1.00 g, 7.21 mmol) and toluene (24 mL). Cool the resulting solution at 0° C. and add DIBAL-H (1.0 M in toluene, 7.58 mL, 7.58 mmol) dropwise. Stir the resulting red solution at 0° C. for 1 h. Then, add methanol (2 mL) followed by H2SO4 (aq. 2.0 M, 6 mL). Stir for 1 h at rt. Add CHCl3:isopropanol (3/1, 15 mL) and wash with Rochelle's salt solution (20 mL), followed by NaHCO3 (20 mL) and brine. Dry the combined organic layers over magnesium sulfate, filter and concentrate. Purify by flash chromatography (EtOAc/hexanes 10%) to give the title compound (530 mg, 62%).

후처리

  1. stirringStir for 1 h at rt
  2. washAdd CHCl3:isopropanol (3/1, 15 mL) and wash with Rochelle's salt solution (20 mL)
  3. dry with materialDry the combined organic layers over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify by flash chromatography (EtOAc/hexanes 10%)

출처 및 근거

ORD 기록
ord-11f65d50ccb94616be56241ee9ec4429
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381719B2

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