Hydroxyamine hydrochloride → HCID 178438356, compound

HRID 1265236Notes

Reaction equation

HRID 1265236 reaction equation
[CH2:1]([C:4]1[C:5]([C:18]([C:20]2[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=2)=[O:19])=[CH:6][C:7]2[C:8]([CH3:17])([CH3:16])[CH2:9][CH2:10][C:11]([CH3:15])([CH3:14])[C:12]=2[CH:13]=1)[CH2:2][CH3:3].Cl.[NH2:30][OH:31]>CCO.N1C=CC=CC=1>[CH2:1]([C:4]1[C:5]([C:18]([C:20]2[CH:28]=[CH:27][C:23]([C:24](=[N:30][OH:31])[OH:25])=[CH:22][CH:21]=2)=[O:19])=[CH:6][C:7]2[C:8]([CH3:17])([CH3:16])[CH2:9][CH2:10][C:11]([CH3:15])([CH3:14])[C:12]=2[CH:13]=1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 10022568HCID 10022568, compound

Product 1

HCID 178438356HCID 178438356, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

4-[(3-n-propyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-napthyl)carbonyl]benzoic acid (101) (12.6 mmol) in EtOH (10 mL) and pyridine (15.3 mL) was treated with hydroxylamine hydrochloride (4.38 g, 63 mmol), and the mixture was heated at reflux. After 6 h, the mixture was cooled to room temperature and the ethanol was removed in vacuo. The residue was taken-up in water and the aqueous layer was adjusted to pH=4-5 with 1 M aqueous HCl. The aqueous solution was extracted with EtOAc, 3×. The organic layers were combined and washed with water (2×) and brine. The organic solution was dried (NaSO4), filtered, and concentrated to give a foamy white solid. Recrystallization (CH2Cl2/ether/hexanes) gave 4-[(3-n-propyl,5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbonyl]benzoic acid oxime (104), as white crystals (85%): mp 255-257°C.; 1H-NMR (400 MHz, CDCl3) δ8.19 (½ABq, J=8.3 Hz, 2H, ArH), 7.89 (½ABq, J=8.3 Hz, 2H, ArH), 7.23 (s, 1H, ArH), 7.20 (s, 1H, ArH), 2.65 (m, 2H, CH2), 1.70 (m, 4H, 2CH2), 1.56 (m, 2H, CH2), 1.32 (s, 6H, 2CH3) 1.20 (s, 6H, 2CH3), 0.88 (t, J=7.3 Hz, 3H, CH3).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. customthe ethanol was removed in vacuo
  4. extractionThe aqueous solution was extracted with EtOAc, 3×
  5. washwashed with water (2×) and brine
  6. dry with materialThe organic solution was dried (NaSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a foamy white solid
  10. customRecrystallization (CH2Cl2/ether/hexanes)

Sources & evidence

ORD record
ord-56ab46fa7513401ba9f8bbd7f76982f3
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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