Methanol → 6-(Methylamino)nicotinaldehyde

HRID 534775노트

반응식

HRID 534775 반응식
[CH3:1][NH:2][C:3]1[N:8]=[CH:7][C:6]([C:9]#N)=[CH:5][CH:4]=1.CC(C[Al]CC(C)C)C.CO.[OH:22]S(O)(=O)=O>C1(C)C=CC=CC=1>[CH3:1][NH:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=[O:22])=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 16682954DibahHCID 178608996-(Methylamino)pyridine-3-carbonitrile

생성물 1

HCID 184162986-(Methylamino)nicotinaldehyde

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
-78 °C

실험 절차

To 6-(methylamino)-3-pyridinecarbonitrile (D94) (0.1 g, 0.752 mmol) in toluene (10 mL) cooled to −78 C under argon was added Dibal-H (1.88 mL, 1M solution in toluene, 11.2 mmol) dropwise. The reaction was stirred at −78° C. and then allowed to warm to room temperature overnight. MeOH (0.47 mL) and 2 M H2SO4 (1.42 mL) were added and mixture was stirred for 1.5 h then concentrated in vacuo. The residue was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were dried and concentrated to give the title compound (0.067 g). δH (CDCl3, 400 MHz) 9.78 (1H, s), 8.52 (1H, d), 7.92 (1H, dd), 6.45 (1H, d), 5.38 (1H, br.s), 3.04 (3H, d). MS (ES): MH+ 137.1.

후처리

  1. temperatureto warm to room temperature overnight
  2. stirringmixture was stirred for 1.5 h
  3. concentrationthen concentrated in vacuo
  4. customThe residue was partitioned between water and EtOAc
  5. extractionThe aqueous layer was extracted with EtOAc
  6. customthe combined organic layers were dried
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-055b213759f34416bed1dfd49fc46710
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853218B2

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