Hydroxyamine hydrochloride → HCID 76779877, compound

HRID 1049094Notes

Reaction equation

HRID 1049094 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[CH3:14])(=O)[CH3:2].Cl.[NH2:16][OH:17].C([O-])(=O)C.[Na+]>CO>[OH:17][N:16]=[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[CH3:14])[CH3:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 20665294Methyl 4-acetyl-3-methylbenzoate

Product 1

HCID 76779877HCID 76779877, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

Methyl 4-acetyl-3-methylbenzoate (1.49 g, 7.76 mmol), hydroxylamine hydrochloride (4.18 g, 60.1 mmol), and sodium acetate (4.93 g, 60.1 mmol) were suspended in methanol (40 mL) and the reaction mixture heated at 40° C. for 2 h. Upon cooling to room temperature the solvent was removed under reduced pressure. The residue obtained was partitioned between ethyl acetate (75 mL) and water (30 mL). The organic extract was washed with water (20 mL) and brine. The washed extract was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound as a solid (1.61 g, 100%). LC-MS: (FA) ES+ 208; 1H NMR (300 MHz, MeO D) δ 7.91-7.77 (m, 2H), 7.31 (d, J=8.0 Hz, 0.7H), 7.16 (d, J=7.9 Hz, 0.3H), 3.89 (s, 3H), 2.37 (s, 2H), 2.28 (s, 1H), 2.17 (s, 2H), 2.10 (s, 1H).

Workup

  1. temperatureUpon cooling to room temperature the solvent
  2. customwas removed under reduced pressure
  3. customThe residue obtained
  4. customwas partitioned between ethyl acetate (75 mL) and water (30 mL)
  5. extractionThe organic extract
  6. washwas washed with water (20 mL) and brine
  7. extractionThe washed extract
  8. dry with materialwas dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e158915b1b22449595063aabda18a7b3
Source dataset
uspto-grants-2016_07
Patent number
US09382197B2

Reaction notes

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