3,5-Dichlorosalicylaldehyde → HCID 178449920, compound

HRID 1531247Notes

Reaction equation

HRID 1531247 reaction equation
Cl.[C:2]([NH:6][OH:7])([CH3:5])([CH3:4])[CH3:3].C[O-].[Na+].[Cl:11][C:12]1[C:13]([OH:21])=[C:14]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[CH:15]=O>CO.Cl>[Cl:11][C:12]1[C:13]([OH:21])=[C:14]([CH:15]=[N+:6]([C:2]([CH3:5])([CH3:4])[CH3:3])[O-:7])[CH:17]=[C:18]([Cl:20])[CH:19]=1

Participants

6

Reactant 3

HCID 666603,5-DichlorosalicylaldehydeHCID 2777896N-tert-butylhydroxylamine hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 178449920HCID 178449920, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butylhyroxylamine hydrochloride (1.5 eq.) and sodium methoxide (1.2 eq.) in MeOH was added 3,5-dichloro-2-hydroxybenzaldehyde (1 eq.) and 5 drops of 37% HCl. The resulting solution was refluxed over molecular sieves (40 g) until no more aldehyde was detected by TLC. The mixture was then cold filtered to remove molecular sieves and sodium chloride, and rinsed with CH2Cl2. The solvent was removed in vacuo and the title compound was isolated in 97.1% yield as a yellow crystalline solid, m.p. 102.9° C. (Rf=0.33 on a silica gel plate using 7:3 hexanes/EtOAc as an eluant).

Workup

  1. filtrationThe mixture was then cold filtered
  2. customto remove molecular sieves and sodium chloride
  3. washrinsed with CH2Cl2
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f79eaa9cf6b847b4a392cf56cca09546
Source dataset
uspto-grants-2001_03
Patent number
US06197826B1

Reaction notes

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