Hydroxyamine hydrochloride → HCID 57461144, compound

HRID 2066839Notes

Reaction equation

HRID 2066839 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.[OH2:19].O.O.C([O-])(=O)C.[Na+].Cl.[NH2:28]O>C(O)C.O>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][C:15](=[N:28][OH:19])[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 23665404Sodium Acetate TrihydrateHCID 57461143HCID 57461143, compound

Product 1

HCID 57461144HCID 57461144, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Compound 1b (341 mg, 1.3 mmol) and sodium acetate trihydrate (513 mg, 3.8 mmol) were combined in ethanol (5 mL) and heated to reflux for 15 minutes. Hydroxylamine hydrochloride (131 mg, 1.9 mmol) was added and heating was continued for 3 h. The mixture was cooled to room temperature and diluted with water (30 mL). The mixture was chilled in an ice-bath and the resulting white precipitate was isolated by filtration, washed with water, and dried under vacuum to afford 266 mg (74%) of 1c: 1H NMR (300 MHz, CDCl3) δ 7.98 (br s, 1 H), 7.65-7.56 (m, 2 H), 7.02 (t, J=8.4 Hz, 1 H), 3.42-3.33 (m, 4 H), 3.04 (s, 3 H), 2.82 (t, J=5.9 Hz, 2 H), 2.54 (t, J=5.7 Hz, 2 H); LC-MS 287.1 (MH+).

Workup

  1. temperatureheated
  2. temperatureto reflux for 15 minutes
  3. temperatureheating
  4. temperatureThe mixture was chilled in an ice-bath
  5. customthe resulting white precipitate was isolated by filtration
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-8de9ddf91c084b3f8bf1b1072c963ec6
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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