Lithium → N-methyl-2-phenoxyaniline

HRID 598916ノート

反応式

HRID 598916 の反応式
[O:1]([C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[NH:10][C:11](OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]>O1CCCC1>[CH3:11][NH:10][C:9]1[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=1[O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 3028194LithiumHCID 65142714HCID 65142714、化合物

生成物 1

HCID 22961955N-methyl-2-phenoxyaniline収率 94.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
65 °C

実験手順

To a solution of 2-phenoxy-N-(t-butoxycarbonyl)aniline (1.43 g, 5.0 mmol) in anhydrous tetrahydrofuran (50 ml) was added lithium aluminumhydride (10 ml, 10.0 mmol, 1.0 M solution in tetrahydrofuran) at −10° C. The mixture was then refluxed at 65° C. overnight. The reaction mixture was quenched with slow addition of MeOH (10 ml) and concentrated under reduced pressure. The reaction mixture was then poured into water (50 ml) and extracted with ethyl acetate (3×100 ml). Organic extracts were combined and washed with brine (2×100 ml) and dried over (Na2SO4), concentrated under reduced pressure to give N-methyl-2-phenoxyaniline (0.94 g, 94.0%) as a pale yellow oil. The product was confirmed by LC-MS and subjected to next reaction without further purification.

後処理

  1. customThe reaction mixture was quenched with slow addition of MeOH (10 ml)
  2. concentrationconcentrated under reduced pressure
  3. additionThe reaction mixture was then poured into water (50 ml)
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. washwashed with brine (2×100 ml)
  6. dry with materialdried over (Na2SO4)
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-c099294b387141bb9d498267ae6a007e
出典データセット
uspto-grants-2011_03
特許番号
US07897628B2

反応ノート

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