Hydrochloric Acid → N-(2-chloro-3-methoxyphenyl)-2-hydroxyimino-acetamide

HRID 388684Notes

Reaction equation

HRID 388684 reaction equation
S([O-])([O-])(=O)=O.[Na+].[Na+].Cl[C:9](Cl)(Cl)[CH:10]([OH:12])O.Cl.[Cl:16][C:17]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19].Cl.[NH2:27][OH:28]>O>[Cl:16][C:17]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[CH:20][C:18]=1[NH:19][C:10](=[O:12])[CH:9]=[N:27][OH:28]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 2707Chloral HydrateHCID 24436Sodium SulfateHCID 248201302-Chloro-3-methoxyaniline hydrochloride

Product 1

HCID 86633207N-(2-chloro-3-methoxyphenyl)-2-hydroxyimino-acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred solution of sodium sulfate (58.5 g, 412 mmol) in water (100 mL) was added a solution of chloralhydrate (9.36 g, 56.6 mmol) in water (120 mL). Chloroanisidine 215d (10 g, 51.5 mmol) was added followed by 37% HCl (20 mL). A solution of hydroxylamine (50% in water, 4.7 mL, 154.5 mmol) in 50 mL was then added and the reaction mixture was refluxed for 90 min. The suspended solid was filtered off, and washed with water and ether. Organics were dried over Na2SO4, filtered, and concentrated under reduced pressure to yield compound 245d as a brown solid. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 3.86 (s, 3H), 6.98 (d, J=8.07 Hz, 1H), 7.31 (t, J=8.07 Hz, 1H), 7.61 (d, J=8.07 Hz, 1H), 7.66 (s, 1H), 9.43 (s, 1H), 12.43 (s, 1H).

Workup

  1. temperaturethe reaction mixture was refluxed for 90 min
  2. filtrationThe suspended solid was filtered off
  3. washwashed with water and ether
  4. dry with materialOrganics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3894ded36a25460f8c01b253f3c5bce7
Source dataset
uspto-grants-2013_02
Patent number
US08377962B2

Reaction notes

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