2-Nitroaniline → N-(4-methoxybutyl)-2-nitroaniline

HRID 1475175ノート

反応式

HRID 1475175 の反応式
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[Br-].[K+].Cl[CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH3:19].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:19][O:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[N+:1]([O-:3])=[O:2]

参加物

7

反応物 4

HCID 69462-NitroanilineHCID 14798Sodium HydroxideHCID 873631-Chloro-4-methoxybutaneHCID 253877Potassium Bromide

生成物 1

HCID 60964965N-(4-methoxybutyl)-2-nitroaniline収率 100%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒2 回

反応条件

温度
90 °C

実験手順

Toluene (500 mL) was added to o-nitroaniline (50.0 g, 0.362 mol), tetrabutylammonium bromide (58.3 g, 0.181 mol) and potassium bromide (43.1 g, 0.362 mol). 1-Chloro-4-methoxybutane (66.6 g, 0.543 mol) and 50 w/v % aqueous sodium hydroxide solution (145 mL, 1.81 mol) were added at 20-30° C. The reaction mixture was heated to 85-95° C., and stirred for 6 hr. After allowing to cool to 20-30° C., the reaction mixture was washed successively with water (250 mL), 1N hydrochloric acid (250 mL×2), 5 w/v % sodium bicarbonate water (250 mL) and water (250 mL). The organic layer was concentrated under reduced pressure to the content (250 mL), and toluene (100 mL) was added to give a toluene solution (350 mL) of N-(4-methoxybutyl)-2-nitroaniline (yield 100%).

後処理

  1. temperatureto cool to 20-30° C.
  2. washthe reaction mixture was washed successively with water (250 mL), 1N hydrochloric acid (250 mL×2), 5 w/v % sodium bicarbonate water (250 mL) and water (250 mL)
  3. concentrationThe organic layer was concentrated under reduced pressure to the content (250 mL), and toluene (100 mL)
  4. additionwas added

出典と根拠

ORDレコード
ord-a65f026791714c46b67632f1f598236d
出典データセット
uspto-grants-2015_04
特許番号
US09018374B2

反応ノート

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