p-Toluenesulfonic acid → HCID 23288677, 화합물

HRID 1430965노트

반응식

HRID 1430965 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1O)[CH:5]=O.[ClH:14].[NH2:15]O.CC1C=CC(S(O)(=O)=O)=CC=1.S([O-])([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1>[Cl:14][C:9]1[C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:4]([C:5]#[N:15])=[CH:3][C:2]=1[OH:1]

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 443297Hydroxyamine hydrochlorideHCID 57489573,4-Dihydroxy-5-nitrobenzaldehyde

생성물 1

HCID 23288677HCID 23288677, 화합물수율 75.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 3,4-dihydroxy-5-nitrobenzaldehyde (5 g, 27.3 mmol), hydroxylamine hydrochloride (2.467 g, 35.5 mmol), tosic acid (0.779 g, 4.10 mmol) and magnesium sulfate (26.3 g, 218 mmol) in toluene (25 ml) was heated at reflux for 6 hours. The reaction mixture was cooled to room temperature, the reaction mixture was partitioned between ethyl acetate and water. The layers were separated and aqueous layer was extracted with ethyl acetate two more times. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo to a small volume and a brown precipitate formed. the precipitate was collected by filtration and after drying under vacuum to give 4.1 g of 4-chloro-3-hydroxy-5-nitrobenzonitrile.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. customthe reaction mixture was partitioned between ethyl acetate and water
  4. customThe layers were separated
  5. extractionaqueous layer was extracted with ethyl acetate two more times
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo to a small volume
  10. customa brown precipitate formed
  11. filtrationthe precipitate was collected by filtration
  12. customafter drying under vacuum

출처 및 근거

ORD 기록
ord-7c37bc9dc32749778e0d622be801c9c2
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940736B2

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