Sulfuric acid magnesium salt (1:1) → HCID 23288677、化合物

HRID 921786ノート

反応式

HRID 921786 の反応式
[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.C1(C)C=CC(CS(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]

参加物

6

反応物 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 443297Hydroxyamine hydrochlorideHCID 57489573,4-Dihydroxy-5-nitrobenzaldehydeHCID 10149049(4-methylphenyl)methanesulfonic Acid

生成物 1

HCID 23288677HCID 23288677、化合物収率 75.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 3,4-dihydroxy-5-nitrobenzaldehyde (5 g, 27.3 mmol), hydroxylamine hydrochloride (2.467 g, 35.5 mmol), p-toluenemethanesulfonic 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.

後処理

  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

出典と根拠

ORDレコード
ord-57972196ad4b4a049a2ef1b884050d4f
出典データセット
uspto-grants-2016_03
特許番号
US09273057B2

反応ノート

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