3,4-Dichlorobenzaldehyde → 5331-92-0

HRID 1106698Notes

Reaction equation

HRID 1106698 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH:5]=O.Cl.[NH2:12][OH:13]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH:5]=[N:12][OH:13]

Participants

4

Reactant 2

HCID 227103,4-DichlorobenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 2207415331-92-0Yield 101.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,4-Dichlorobenzaldehyde (5.25 g) and 2.1 g of hydroxylamine hydrochloride were dissolved in 75 mL of pyridine. The mixture was stirred at room temperature for 18 h. The solvent was removed in vacuo and the residue was taken up in 100 mL of 1N HCl and extracted 3× with 75 mL portions of ethyl acetate. The combined organic extracts were dried (MgSO4), filtered, and concentrated to give a solid. The crude material was triturated in hexane and collected by filtration to yield 5.8 g of the title compound of Step A as a white solid melting at 118-119° C.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionextracted 3× with 75 mL portions of ethyl acetate
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a solid
  7. customThe crude material was triturated in hexane
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-7c97e64c390d4013ba578e282955cfa4
Source dataset
uspto-grants-2000_05
Patent number
US06057352

Reaction notes

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