Lithium → N-methyl-2-phenoxyaniline

HRID 559831노트

반응식

HRID 559831 반응식
[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

참가 물질

4

반응물 2

HCID 3028194LithiumHCID 65142714HCID 65142714, 화합물

생성물 1

HCID 22961955N-methyl-2-phenoxyaniline수율 94.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
65 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-57661183dc00426484efe06d0b3c6b81
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063081B2

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