Ethanolamine → 2-(2-Hydroxyethylamino)-3-nitrobenzoic acid

HRID 1991189ノート

反応式

HRID 1991189 の反応式
Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:14]([CH2:16][NH2:17])[OH:15]>C(O)C>[OH:15][CH2:14][CH2:16][NH:17][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

参加物

4

反応物 2

HCID 700EthanolamineHCID 198702-Chloro-3-nitrobenzoic acid

生成物 1

HCID 111488352-(2-Hydroxyethylamino)-3-nitrobenzoic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

2-Chloro-3-nitrobenzoic acid (5.0 g, 24.8 mmol) was suspended in ethanol (90 mL) and ethanolamine (4.5 mL, 74.8 mmol) was added. The resulting clear solution was heated at 100° C. for two days. The volatiles were removed under reduced pressure. The residue was treated with water (40 mL) and the mixture was acidified with 1M hydrochloric acid to pH 2. A yellow precipitate formed was collected by filtration and washed with water to yield 2-(2-hydroxyethylamino)-3-nitrobenzoic acid, 5.14 g (92%). MS (ESI) m/z 225 [M−H]. 1H NMR (400 MHz, CD3OD) δ ppm 3.04 (t, J=5.31 Hz, 2H), 3.69 (t, J=5.31 Hz, 2H), 6.71 (t, J=7.96 Hz, 1H), 7.93 (dd, J=8.21, 1.64 Hz, 1H), 8.13 (dd, J=7.71, 1.64 Hz, 1H).

後処理

  1. customThe volatiles were removed under reduced pressure
  2. additionThe residue was treated with water (40 mL)
  3. customA yellow precipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with water

出典と根拠

ORDレコード
ord-709dfe048bf04c9188210331d1c321d9
出典データセット
uspto-grants-2010_01
特許番号
US07645784B2

反応ノート

読み込み中…