Sodium Hydroxide → 2-Amino-4-fluorophenol

HRID 323110

반응식

HRID 323110 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[NH2:9][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[OH:8]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 1362364-Fluoro-2-nitrophenol

생성물 1

HCID 27359172-Amino-4-fluorophenol수율 105.5%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

A mixture of 4-fluoro-2-nitrophenol(1 g, 4.64 mmol) and tin (II) chloride (5.4 g, 24.2 mmol) in ethanol(50 mL) was heated at 80° C. under argon. After 2 hours, the starting material had disappeared and the solution was allowed to cool down and then poured into ice. The pH is made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2Cl2) gave the desired product(622 mg, 85%). 1H NMR (CD3OD): d 6.51 (dd, 1H), 6.32 (dd, 1H), 6.17 (ddd, 1H).

후처리

  1. temperatureto cool down
  2. additionpoured into ice
  3. extractionbefore being extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-718e4150d08e4498bb4f559398606039
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211373B1

연결된 노트

불러오는 중…