1-(2-Hydroxy-3-methylphenyl)ethan-1-one → 6-[1-(Hydroxyamino)ethylidene]-2-methylcyclohexa-2,4-dien-1-one

HRID 873880Notes

Reaction equation

HRID 873880 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=O)[CH3:10].CC([O-])=O.[Na+].Cl.[NH2:18][OH:19]>CO.[Cl-].[Na+].O>[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1/[C:9](=[N:18]/[OH:19])/[CH3:10]

Participants

6

Reactant 3

HCID 2404371-(2-Hydroxy-3-methylphenyl)ethan-1-oneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 1370147826-[1-(Hydroxyamino)ethylidene]-2-methylcyclohexa-2,4-dien-1-oneYield 89.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

1-(2-hydroxy-3-methylphenyl)ethanone (Step 46.1) (900 mg, 5.87 mmol) was dissolved in MeOH (15 mL) and NaOAc (771 mg, 9.40 mmol) and hydroxylamine hydrochloride (612 mg, 8.81 mmol) were successively added. The resulting mixture was heated up and stirred at 60° C. for 2 hr. The reaction mixture was poured into brine and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford the title product (964 mg, 5.25 mmol, 89% yield) as a colorless solid. tR: 0.94 min (LC-MS 2); ESI-MS: 166 [M+H]+, ESI-MS: 164 [M−H]− (LC-MS 2); Rf=0.66 (hexane/EtOAc 1:1).

Workup

  1. temperatureThe resulting mixture was heated up
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2697d2e75fe9400cb9dd7ebee98790f2
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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