Methanol → 2-Methoxyisonicotinonitrile

HRID 238465

反応式

HRID 238465 の反応式
N#N.[CH3:3][OH:4].Cl[C:6]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][N:7]=1>O1CCOCC1.CO>[C:12]([C:10]1[CH:9]=[CH:8][N:7]=[C:6]([O:4][CH3:3])[CH:11]=1)#[N:13]

参加物

5

反応物 3

HCID 887MethanolHCID 947NitrogenHCID 5686382-Chloro-4-cyanopyridine

生成物 1

HCID 72048872-Methoxyisonicotinonitrile

試薬・触媒・溶媒 1

HCID 21966525Dioxane Methanol溶媒

反応条件

温度
10 °C

実験手順

Under a stream of N2 and with cooling, Na metal (2.7 g) was added to MeOH (36 ml) with a considerable exotherm. After the Na is dissolved, a solution of 2-chloro-4-cyanopyridine (15 g) in dioxane:MeOH (1:1, 110 ml) was added via dropping funnel over a 10 min period. The reaction was heated to reflux for 3.5 h then cooled at ˜10° C. overnight. Solid was filtered off and the solid was washed with MeOH. The filtrate was concentrated to ˜60 ml and H2O (60 ml) was added to redissolve a precipitate. Upon further concentration, a precipitate formed which was washed with H2O. Further concentration produced additional solids. The solids were combined and dried in vacuo overnight at 35° C. to provide 4-cyano-2-methoxypyridine which was used as is.

後処理

  1. customover a 10 min
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 3.5 h
  4. filtrationSolid was filtered off
  5. washthe solid was washed with MeOH
  6. concentrationThe filtrate was concentrated to ˜60 ml and H2O (60 ml)
  7. additionwas added
  8. dissolutionto redissolve a precipitate
  9. concentrationUpon further concentration
  10. customa precipitate formed which
  11. washwas washed with H2O
  12. concentrationFurther concentration
  13. customproduced additional solids
  14. customdried in vacuo overnight at 35° C.

出典と根拠

ORDレコード
ord-64dfeb30f56d4b0999f61d5d123fd063
出典データセット
uspto-grants-2014_02
特許番号
US08642624B2

関連ノート

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