Benzyl 2-nitrophenyl ether → 2-Benzyloxyaniline

HRID 350401

반응식

HRID 350401 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 1 N HCl, then acidic solution was alkalified by the addition of 1 N 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) δ 3.71 (broad s , 2H), 5.06 (s, 2H), 6.68–6.86 (m, 4H), 7.32–7.44 (m, 51); FAB-MS m/z 200 (M++1).

후처리

  1. customthe mixture was evaporated off
  2. dissolutionThe black precipitate was dissolved in 1 N HCl
  3. additionacidic solution was alkalified by the addition of 1 N 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-e3cc5964d74646058a5ea2e678406355
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179819B2

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