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

HRID 1475175노트

반응식

HRID 1475175 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 60964965N-(4-methoxybutyl)-2-nitroaniline수율 100%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매2회

반응 조건

온도
90 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a65f026791714c46b67632f1f598236d
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018374B2

반응 노트

불러오는 중…