4-Hydroxybenzaldehyde → 6-(4-Formylphenoxy)nicotinonitrile

HRID 228496ノート

反応式

HRID 228496 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][N:12]=1.C([O-])([O-])=O.[K+].[K+].CC(N(C)C)=O.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][N:12]=2)=[CH:3][CH:4]=1)=[O:7]

参加物

6

反応物 4

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 66603805toluene N,N-dimethylacetamide

生成物 1

HCID 471502166-(4-Formylphenoxy)nicotinonitrile収率 89.9%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Combine 4-Hydroxybenzaldehyde (8.0 g, 65.5 mmol), 6-Chloronicotinonitrile (9.07 g, 65.5 mmol), powdered K2CO3 (13.6 g, 98.3 mmol), and DMA/Toluene (80/240 mL) in a 500 mL RB flask equipped with a stir, reflux condenser and a Dean Stark Trap. Reflux the reaction mixture for several hours under a Nitrogen atmosphere then cool to room temperature and quench with sat NH4Cl (aq). Add Ethyl acetate to extract the product and wash several times with water and then brine. Dry the organic layer over Na2SO4. Concentrate and flash chromatograph using 2:1 Hexanes:Ethyl acetate to give 13.2 g (88% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 7.1 (1H, d), 7.3-7.4 (2H, m), 7.9-8.0 (3H, m), 8.5 (1H, d), 10.0 (1H, s); MS m/z 225 (M+1).

後処理

  1. temperaturereflux condenser
  2. temperatureReflux the reaction mixture for several hours under a Nitrogen atmosphere
  3. customquench with sat NH4Cl (aq)
  4. extractionAdd Ethyl acetate to extract the product
  5. washwash several times with water
  6. dry with materialDry the organic layer over Na2SO4
  7. concentrationConcentrate

出典と根拠

ORDレコード
ord-9aed9d76c31741ec977db8b707c2878d
出典データセット
uspto-grants-2009_07
特許番号
US07560463B2

反応ノート

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