Benzyl 2-nitrophenyl ether → 2-Benzyloxyaniline

HRID 354337

反応式

HRID 354337 の反応式
[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

参加物

5

反応物 2

HCID 736266Benzyl 2-nitrophenyl etherHCID 4311764Sodium borohydride

生成物 1

HCID 2405482-Benzyloxyaniline収率 100%

試薬・触媒・溶媒 2

HCID 24385Nickel Dichloride触媒HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-50a53959db354bfd9338cafbe55baa10
出典データセット
uspto-grants-2004_06
特許番号
US06756378B2

関連ノート

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