Benzoyl chloride → N-Hydroxy-N-methylbenzamide

HRID 2392966Notes

Reaction equation

HRID 2392966 reaction equation
Cl.[CH3:2][NH:3][OH:4].O1C=CC=C(O)C1.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O>[CH3:2][N:3]([C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[OH:4]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 77906N-methylhydroxylamine hydrochlorideHCID 22143352HCID 22143352, compound

Product 1

HCID 371715N-Hydroxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The n-methyl hydroxylamine-HCl and m-pyrol were combined in a 250 milliliter (ml) round bottomed flask, cooled in an ice bath, and allowed to mix until most of the salt dissolved. The benzoyl chloride was slowly added over 15 minutes and allowed to stir for 1 hour. The water was then added and the product extracted three times with ethyl acetate. The ethyl acetate was evaporated from the product, and the product dissolved in 200 ml of 5% NaOH. The product was then extracted three times with 100 ml methylene chloride. The aqueous layer was acidified with H2S04 to a pH of 6 and then extracted three times with 100 ml of ethyl acetate. The organic layer was dried with MgS04 and silica gel, and evaporated to dryness yielding n-methylbenzohydroxamic acid.

Workup

  1. temperaturecooled in an ice bath
  2. additionto mix until most of the salt
  3. dissolutiondissolved
  4. extractionthe product extracted three times with ethyl acetate
  5. customThe ethyl acetate was evaporated from the product
  6. dissolutionthe product dissolved in 200 ml of 5% NaOH
  7. extractionThe product was then extracted three times with 100 ml methylene chloride
  8. extractionextracted three times with 100 ml of ethyl acetate
  9. customThe organic layer was dried with MgS04 and silica gel
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-c46e612fe6164245b1a6573378df9096
Source dataset
uspto-grants-1998_09
Patent number
US05804051

Reaction notes

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