Hydroxyamine hydrochloride → HCID 57523593, compound

HRID 1879095Notes

Reaction equation

HRID 1879095 reaction equation
O[CH:2]=[C:3]1[C:8](=[O:9])[CH:7]=[CH:6][C:5]([CH3:12])([CH:10]=[CH2:11])[CH2:4]1.Cl.[NH2:14]O>C(O)C.O>[CH3:12][C:5]1([CH:10]=[CH2:11])[CH2:4][C:3]2[CH:2]=[N:14][O:9][C:8]=2[CH:7]=[CH:6]1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 67329502HCID 67329502, compound

Product 1

HCID 57523593HCID 57523593, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
115 °C

Procedure

To a stirred solution of 21 (177 mg, 1.078 mmol) in ethanol (15 mL) under a nitrogen atmosphere was added a solution of hydroxylamine hydrochloride (741 mg, 10.66 mmol, 10 eq.) in water (1 mL). The reaction mixture was heated to reflux at 115° C. for 1 hour. Water was then added to the mixture until it became cloudy and the aqueous mixture was extracted with methylene chloride/ethyl ether (1:2, 4×). The organic layers were then combined and washed with saturated sodium bicarbonate solution (1×) and brine (1×), dried over magnesium sulfate, filtered and concentrated in vacuo to give 23 (159.7 mg, 0.99 mmol, 92%) as an oil. The product was used in the next reaction without further purification: 1H NMR (CDCl3) δ 8.03 (1H, s), 6.52 (1H, dd, J=0.6, 10 Hz), 5.87 (1H, d, J=10 Hz), 5.81 (1H, d, J=10.6 Hz), 5.04 (1H, dd, J=0.6, 18.3 Hz), 5.00 (1H, dd, J=1.2, 11.4 Hz), 2.69 (2H, dd, J=16.2, 34.8 Hz) 1.23 (3H, s); 13C NMR (CDCl3) δ 165.0, 148.8, 143.6, 141.6, 114.4, 112.7, 109.5, 40.4, 31.4, 26.0; MS (ESI+) m/z 162.1 [M+H]+, HRMS (ESI+) calcd for C10H11NO+H 162.0919. found 169.0913.

Workup

  1. temperatureThe reaction mixture was heated
  2. extractionthe aqueous mixture was extracted with methylene chloride/ethyl ether (1:2, 4×)
  3. washwashed with saturated sodium bicarbonate solution (1×) and brine (1×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ead88e74883f44efa72ee62adbefe779
Source dataset
uspto-grants-2012_11
Patent number
US08314137B2

Reaction notes

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