Sodium Methoxide → N-isopropyl-2-methoxy-isonicotinamide

HRID 646618ノート

反応式

HRID 646618 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][N:13]=1)[C:5]([NH:7][CH:8]([CH3:10])[CH3:9])=[O:6].[CH3:14][O-:15].[Na+]>CO>[CH:8]([NH:7][C:5](=[O:6])[C:4]1[CH:11]=[CH:12][N:13]=[C:2]([O:15][CH3:14])[CH:3]=1)([CH3:10])[CH3:9]

参加物

4

反応物 2

HCID 10942334Sodium MethoxideHCID 120262122-Chloro-N-isopropylisonicotinamide2 回

生成物 1

HCID 16088055N-isopropyl-2-methoxy-isonicotinamide収率 83.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of 19.44 g 2-chloro-N-isopropyl-isonicotinamide (97.86 mmol) as obtainable from example 12, in 165 mL methanol were added 27.82 g NaOMe (489.3 mmol, 5.0 eq) in four equal portions over 60 min. The solution was then heated to 80° C. and the reaction was monitored by HPLC. After 23 h (<2% area starting material 2-chloro-N-isopropyl-isonicotinamide), the mixture was cooled to room temperature and quenched by addition of 200 mL saturated aqueous NH4Cl. The product was extracted three times with 150 mL, in total 450 mL dichloromethane. The combined organic phases were dried over 40 g Na2SO4 (30 min) and filtered. The filter cake was washed with 80 mL dichloromethane. After removal of solvent in a rotary evaporator (40° C., 22 mbar), the crude product (15.856 g, 83% w/w, HPLC purity 93.7% area) was obtained as a white solid.

後処理

  1. temperaturethe mixture was cooled to room temperature
  2. customquenched by addition of 200 mL saturated aqueous NH4Cl
  3. extractionThe product was extracted three times with 150 mL
  4. dry with materialThe combined organic phases were dried over 40 g Na2SO4 (30 min)
  5. filtrationfiltered
  6. washThe filter cake was washed with 80 mL dichloromethane
  7. customAfter removal of solvent
  8. customin a rotary evaporator (40° C., 22 mbar)

出典と根拠

ORDレコード
ord-66bb852c4dd744bd990929624f96f1c9
出典データセット
uspto-grants-2010_04
特許番号
US07705155B2

反応ノート

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