Chloral Hydrate → 2-hydroxyimino-N-(6-quinolinyl)acetamide

HRID 1387405Notes

Reaction equation

HRID 1387405 reaction equation
Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.[OH2:8].O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].Cl.[NH2:26]O.[NH2:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[CH:34][CH:33]=[CH:32]2.C(=O)(O)[O-].[Na+]>O.Cl.CCO>[OH:8][N:26]=[CH:2][C:3]([NH:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[CH:34][CH:33]=[CH:32]2)=[O:5]

Participants

9

Reactant 5

HCID 2707Chloral HydrateHCID 113736-AminoquinolineHCID 62649Sodium sulfate decahydrateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 734148442-hydroxyimino-N-(6-quinolinyl)acetamideYield 69.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 10.0 g (60.0 mmol) of chloral hydrate in 250 mL of water was added 70.0 g (220 mmol) of sodium sulfate decahydrate, followed by a solution of 11.8 g (170 mmol) of hydroxylamine hydrochloride in 100 mL of water. A solution of 7.8 g (54 mmol) of 6-aminoquinoline in 200 mL of 1.0 N HCl was then added with stirring. The resulting suspension was warmed, and 400 mL of 95% EtOH was added to dissolve the suspension. The solution was refluxed for 0.75 h and then cooled to ambient temperature. The solution was neutralized with addition of solid sodium bicarbonate, and the resulting solid was collected by vacuum filtration and air dried to afford 8.1 g (60%) of 2-hydroxyimino-N-(6-quinolinyl)acetamide as a solid: 1H NMR (DMSO-d6): 7.76 (s, 1H); 7.80 (dd, 1H, J=3.7, 8.4 Hz); 8.14 (s, 2H); 8.68 (s, 1H); 8.77 (d, 1H, J=8.4 Hz); 9.02 (d, 1H, J=3.7 Hz); 10.73 (s, 1H); 12.34 (s, 1H). Mass spectrum (negative ion chemical ionization): m/z=214 (60%).

Workup

  1. temperatureThe resulting suspension was warmed
  2. dissolutionto dissolve the suspension
  3. temperatureThe solution was refluxed for 0.75 h
  4. filtrationthe resulting solid was collected by vacuum filtration and air
  5. customdried

Sources & evidence

ORD record
ord-d4379efb20df4253a7ad6f798669c39e
Source dataset
uspto-grants-2001_07
Patent number
US06268391B1

Reaction notes

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