Benzyl 2-nitrophenyl ether → 2-Benzyloxyaniline

HRID 354337

반응식

HRID 354337 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.Cl[Ni]Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 736266Benzyl 2-nitrophenyl etherHCID 4311764Sodium borohydride

생성물 1

HCID 2405482-Benzyloxyaniline수율 100%

시약·촉매·용매 2

HCID 24385Nickel Dichloride촉매HCID 887Methanol용매

실험 절차

To a stirred solution of 2-benzyloxynitrobenzene (9.92 g, 43.3 mmol) and NiCl2 (20.3 g, 157 mmol) in MeOH (350 mL) was added portionwise NaBH4 (8.09 g, 214 mmol) at 0° C. After disappearing of the starting material (monitored by TLC), the mixture was evaporated off. The black precipitate was dissolved in 1N HCl, then acidic solution was alkalified by the addition of 1N NaOH and extracted with EtOAc. The extracts were washed brine, dried over Na2SO4, and concentrated to dryness. Chromatography of the residue with CHCl3 as eluent gave 2-benzyloxy aniline (8.60 g, 100%) as a reddish oil. 1H-NMR (CDCl3) δ3.71 (broad s, 2H), 5.06 (s, 2H), 6.68-6.86 (m, 4H), 7.32-7.44 (m, 5H); FAB-MS m/z 200 (M++1).

후처리

  1. customthe mixture was evaporated off
  2. dissolutionThe black precipitate was dissolved in 1N HCl
  3. additionacidic solution was alkalified by the addition of 1N NaOH
  4. extractionextracted with EtOAc
  5. washThe extracts were washed brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-50a53959db354bfd9338cafbe55baa10
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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