5-Chloro-salicylaldehyde → HCID 178449919, compound

HRID 1531238Notes

Reaction equation

HRID 1531238 reaction equation
[C:1]([NH:5][OH:6])([CH3:4])([CH3:3])[CH3:2].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([OH:16])=[C:12]([CH:15]=1)[CH:13]=O>CO.Cl>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([OH:16])=[C:12]([CH:13]=[N+:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[O-:6])[CH:15]=1

Participants

5

Reactant 2

HCID 124815-Chloro-salicylaldehydeHCID 98586N-tert-butylhydroxylamine

Product 1

HCID 178449919HCID 178449919, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butylhydroxylamine (14.98 g, 168.4 mmol) in MeOH (160 mL) was added 5-chloro-2-hydroxybenzaldehyde (15.8 g, 129.5 mmol) and 3 drops of 37% hydrochloric acid. The resulting solution was refluxed through a Soxhlet apparatus containing molecular sieves (40 g) until no more aldehyde was detected by TLC. The solvent was removed in vacuo and the residue was recrystallized from EtOAc. The title compound was isolated in 98.5% yield as a crystalline solid, m.p. 143.4° C. (Rf=0.45 on a silica gel plate using 7:10 hexanes:EtOAc as an eluant).

Workup

  1. temperatureThe resulting solution was refluxed through a Soxhlet apparatus
  2. customThe solvent was removed in vacuo
  3. customthe residue was recrystallized from EtOAc

Sources & evidence

ORD record
ord-37425a240e7c4c7f8380f66f99c525a9
Source dataset
uspto-grants-2001_03
Patent number
US06197826B1

Reaction notes

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