5-Chloro-salicylaldehyde → 5-Chloro-2-hydroxybenzonitrile

HRID 1160485Notes

Reaction equation

HRID 1160485 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=O.[NH2:11]OS(O)(=O)=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[C:7]#[N:11]

Participants

4

Reactant 2

HCID 124815-Chloro-salicylaldehydeHCID 76284hydroxylamine-O-sulfonic acid

Product 1

HCID 27774205-Chloro-2-hydroxybenzonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

5-chloro-2-hydroxybenzaldehyde (300 g, 1.92 mol) and hydroxylamine-O-sulfonic acid (260 g, 2.30 mol) were suspended in water (4.5 L) at room temperature, which was then stirred at 60° C. for 7 hours. Water (3 L) was added to the reaction mixture, which was then cooled with ice, followed by filtering a crystal before further washing with water (1.5 L). The precipitated crystal was suspended in water (1.5 L), filtered, washed with water, and subjected to tray drying at 50° C. for 22 hours to obtain 272 g of the title compound (white crystal, yield: 93%).

Workup

  1. temperaturewas then cooled with ice
  2. filtrationby filtering a crystal
  3. washbefore further washing with water (1.5 L)
  4. filtrationfiltered
  5. washwashed with water
  6. customdrying at 50° C. for 22 hours

Sources & evidence

ORD record
ord-29d112564158463bad720072bdd0bc0d
Source dataset
uspto-grants-2010_10
Patent number
US07816405B2

Reaction notes

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