Methanol → 6-(Methylamino)nicotinaldehyde

HRID 534775ノート

反応式

HRID 534775 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 184162986-(Methylamino)nicotinaldehyde

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-055b213759f34416bed1dfd49fc46710
出典データセット
uspto-grants-2014_10
特許番号
US08853218B2

反応ノート

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