Hydroxyamine hydrochloride → HCID 57523624, compound

HRID 1879093Notes

Reaction equation

HRID 1879093 reaction equation
O[CH:2]=[C:3]1[C:8](=[O:9])[C:7]([CH3:11])([CH3:10])[CH2:6][C:5]([CH3:13])([CH3:12])[CH2:4]1.Cl.[NH2:15]O>C(O)C.O>[CH3:12][C:5]1([CH3:13])[CH2:4][C:3]2[CH:2]=[N:15][O:9][C:8]=2[C:7]([CH3:11])([CH3:10])[CH2:6]1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 67113925HCID 67113925, compound

Product 1

HCID 57523624HCID 57523624, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
110 °C

Procedure

Under a nitrogen atmosphere and with stirring, a solution of 16 (140 mg, 0.77 mmol) in ethanol (19.1 mL) was added to a solution of hydroxylamine hydrochloride (7.98 mmol, 555 mg, 10.4 eq) in water (980 μL) at room temperature. The mixture was heated to 110° C. and stirred at reflux for 1 hour. After heating, the reaction mixture was diluted with water (10 mL) and the aqueous layer was extracted with methylene chloride/ethyl ether (1:2, 3×10 mL). The organic layers were then combined and washed with saturated aqueous sodium bicarbonate solution (1×12 mL) and brine (2×12 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to give 17 as a yellow oil (122 mg, 0.68 mmol, 89%). The material was used in the next reaction without further purification: 1H NMR (CDCl3) δ 8.00 (1H, s), 2.24 (2H, s), 1.60 (2H, s), 1.34 (6H, s), 1.03 (6H, s); 13C NMR (CDCl3) δ 173.2, 150.0, 110.4, 52.4, 34.4, 32.6, 32.4, 29.7, 29.3. MS: No molecular ion peak is observed by ESI+ and EI methods.

Workup

  1. stirringstirred
  2. temperatureat reflux for 1 hour
  3. temperatureAfter heating
  4. extractionthe aqueous layer was extracted with methylene chloride/ethyl ether (1:2, 3×10 mL)
  5. washwashed with saturated aqueous sodium bicarbonate solution (1×12 mL) and brine (2×12 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a4eb1ef6d084729a0b3b90ed9c976e1
Source dataset
uspto-grants-2012_11
Patent number
US08314137B2

Reaction notes

Loading…