Hydrochloric Acid → N-Hydroxy-N-methylbenzamide

HRID 1197919Notes

Reaction equation

HRID 1197919 reaction equation
Cl.[CH3:2][NH:3][OH:4].N1C=CC=CC=1.[C:11](Cl)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>O1CCCC1>[C:11]([N:3]([CH3:2])[OH:4])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7412Benzoyl chlorideHCID 77906N-methylhydroxylamine hydrochloride

Product 1

HCID 371715N-Hydroxy-N-methylbenzamideYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10.0 g of N-methylhydroxylamine hydrochloride was added to 100 ml of tetrahydrofuran and 19.8 g of pyridine was added to the mixture. To the resulting mixture, there was dropwise added a solution of 16.8 g of benzoyl chloride in 100 ml of tetrahydrofuran at room temperature over one hour with stirring. The stirring was continued for additional 8 hours to proceed the reaction. After addition of 50 ml of dilute hydrochloric acid, the tetrahydrofuran was removed in vacuo and the remaining solution was extracted with ethyl acetate. The resultant extract was dried over anhydrous magnesium sulfate and then the ethyl acetate was removed under reduced pressure. The crude product obtained was purified by column chromatography (packed material: silica gel; eluent: ethyl acetate/hexane) to give 8.5 g of N-benzoyl-N-methylhydroxylamine as an oil having a melting point of not more than 20° C.

Workup

  1. additionwas added to the mixture
  2. customthe reaction
  3. customthe tetrahydrofuran was removed in vacuo
  4. extractionthe remaining solution was extracted with ethyl acetate
  5. extractionThe resultant extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customthe ethyl acetate was removed under reduced pressure
  8. customThe crude product obtained
  9. customwas purified by column chromatography (packed material: silica gel; eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4dce8d254ea641e7bc98a089556f1296
Source dataset
uspto-grants-1994_01
Patent number
US05278273

Reaction notes

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