4-Chloroaniline → HCID 57289360, 화합물

HRID 28670

반응식

HRID 28670 반응식
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[N:9]([O-])=O.[Na+].OC=[C:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]1=[O:21].C([O-])(=O)C.[Na+]>Cl.O.CO>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][N:9]=[C:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]2=[O:21])=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 78124-ChloroanilineHCID 101871Cyclohexanone, 2-(hydroxymethylene)-HCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

생성물 1

HCID 57289360HCID 57289360, 화합물수율 49%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 887Methanol용매HCID 962Water용매2회

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온도
0 °C

실험 절차

To a cold (0° C.) solution of 4-chloroaniline (5.6 g, 44 mmol) in concentrated hydrochloric acid (5 mL) was added sodium nitrite (3.0 g, 44 mmol) dissolved in water (10 mL) portionwise over 20 minutes. The mixture was stirred at 0° C. for 30 minutes. In a separate flask, a cool solution of 2-(hydroxymethylene)cyclohexanone (Organic Syntheses, Collective Vol 4, 1963, pg. 536) (5.0 g, 40 mmol) in methanol (30 mL) was treated with a solution of sodium acetate (8.3 g, 101 mmol) in water (25 mL). The mixture was stirred at 0° C. for 20 minutes and the diazonium salt slurry was added. The combined mixture was stirred for 10-15 minutes, collected by filtration, triturated with ethanol, and collected by filtration to give cyclohexane-1,2-dione (4-chlorophenyl)hydrazone (4.6 g, 49% yield) as a yellow solid. 1H-NMR (DMSO-d6): δ 9.93 (s, 1H), 7.29 (m, 4H), 2.55 (m, 2H), 2.40 (m, 2H), 1.84-1.75 (m, 4H).

후처리

  1. stirringThe mixture was stirred at 0° C. for 20 minutes
  2. stirringThe combined mixture was stirred for 10-15 minutes
  3. filtrationcollected by filtration
  4. customtriturated with ethanol
  5. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-1d2fae41e866434da2bf685100ac5eb4
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419997B2

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