Sulfuric acid magnesium salt (1:1) → HCID 23288677, compound

HRID 921786Notes

Reaction equation

HRID 921786 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 23288677HCID 23288677, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-57972196ad4b4a049a2ef1b884050d4f
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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