Ethanolamine → 2-[(2-Bromo-6-nitrophenyl)amino]ethanol

HRID 1991183ノート

反応式

HRID 1991183 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1Cl.[CH2:12]([CH2:14][NH2:15])[OH:13]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[NH:15][CH2:14][CH2:12][OH:13]

参加物

4

反応物 2

HCID 700EthanolamineHCID 227360531-Bromo-2-chloro-3-nitrobenzene

生成物 1

HCID 112539952-[(2-Bromo-6-nitrophenyl)amino]ethanol

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 1-bromo-2-chloro-3-nitrobenzene (0.34 g, 1.4 mmol) and ethanolamine (0.22 mL, 3.5 mmol) in dry ethanol (3.8 mL) was irradiated in a microwave oven at 135° C. for 180 min. After the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, the organic phase was washed with potassium bisulfate (0.1 M), water and brine, dried over Na2SO4 and concentrated. Purification was performed using flash chromatography on a silica column and 25% ethyl acetate in heptane as an eluent to yield 2-[(2-bromo-6-nitrophenyl)amino]ethanol as red oil, 0.24 g (65%). 1H NMR (400 MHz, DMSO-D6) δ ppm 3.13 (q, J=5.2 Hz, 2H) 3.51 (q, J=5.1 Hz, 2H) 4.87 (t, J=5.1 Hz, 1H) 6.18 (t, J=5.1 Hz, 1H) 6.80 (t, J=8.1 Hz, 1H) 7.84 (dd, J=7.8, 3.3 Hz, 2H).

後処理

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe organic phase was washed with potassium bisulfate (0.1 M), water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification

出典と根拠

ORDレコード
ord-5e4723329dd040d5b5e24717915fd1c3
出典データセット
uspto-grants-2010_01
特許番号
US07645784B2

反応ノート

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