Water → 1,2-Bis(3-chlorophenyl)hydrazine

HRID 266676

반응식

HRID 266676 반응식
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([N+:10]([O-])=O)[CH:7]=[CH:8][CH:9]=1.O>[Zn].CCOCC>[Cl:3][C:4]1[CH:5]=[C:6]([NH:10][NH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[CH:5]=2)[CH:7]=[CH:8][CH:9]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 84891-Chloro-3-nitrobenzeneHCID 14798Sodium Hydroxide2회

생성물 1

HCID 2579191,2-Bis(3-chlorophenyl)hydrazine수율 68.5%

시약·촉매·용매 2

HCID 23994Zinc촉매2회HCID 3283Diethyl Ether용매

반응 조건

온도
60 °C

실험 절차

To a stirred solution of 50% NaOH (3 mL) was added 3-chloronitrobenzene (10 g, 64 mM). The suspension was warmed to 60° C. and zinc (9 g, 138 mM) was added. During the addition, the temperature of the reaction mixture was kept between 60° and 80° C. After the addition was complete, a solution of 20% NaOH (18 mL, 90 mM) was added followed by water (30 mL). An additional portion of zinc (12 g, 189 mM) was then added and the resulting mixture was stirred between 75°-80° C. for 2 hours. After cooling to room temperature, the mixture was added to ether (200 mL), stirred, and the liquid was decanted. The solids were then resuspended in ether and the extraction was repeated 3 times. The ether extracts were combined, dried (Na2SO4), and concentrated to give a yellow solid. This was purified by flash column chromatography using CH2Cl2 as elutant which afforded the titled compound as a yellow solid (5.5 g, 68%). NMR (CDCl3): 7.12 (t, J=8 Hz, 2H), 6.80 (m, 4H), 6.67 (dd, J1 =1 Hz, J2 =8 Hz, 2H), 5.66 (br s, 2H).

후처리

  1. additionDuring the addition
  2. customwas kept between 60° and 80° C
  3. additionAfter the addition
  4. temperatureAfter cooling to room temperature
  5. stirringstirred
  6. customthe liquid was decanted
  7. extractionthe extraction
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customto give a yellow solid
  11. customThis was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-849d6f9dce954ca088376be8c11a50e5
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05652239

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