Hydrochloric Acid → N-Hydroxy-N-methylbenzamide

HRID 1758018Notes

Reaction equation

HRID 1758018 reaction equation
[CH3:1][N:2]([O:11]C(=O)C1C=CC=CC=1)[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].Cl>O>[OH:11][N:2]([CH3:1])[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12593591HCID 12593591, compound

Product 1

HCID 371715N-Hydroxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask equipped with a stirrer and a heating mantle were added N-methyl-N-benzoyloxybenzamide (29.2 g, 0.119 mol) from above, 100 mL of water, and 10 g of sodium hydroxide. The mixture was stirred well and heated to 70°. A clear solution was obtained in 30 min. After a total of 45 min the solution was cooled and concentrated hydrochloric acid was added to bring the solution to pH 7. The mixture was extracted with methylene chloride, and the organic layer was dried, first with magnesium sulfate and then with 4 A molecular sieves. Evaporation of the solvent gave 14.7 g (81%) of colorless, liquid, N-hydroxy-N-methylbenzamide; nmr (CDCl3) 9.67 (broad s, CH, 1H), 7.7-7.1 (m, 5H), 3.20 (s, 3H). Attempts to vacuum distill the product were unsuccessful because of thermal decomposition.

Workup

  1. customTo a flask equipped with a stirrer
  2. temperatureheated to 70°
  3. customA clear solution was obtained in 30 min
  4. temperatureAfter a total of 45 min the solution was cooled
  5. extractionThe mixture was extracted with methylene chloride
  6. dry with materialthe organic layer was dried, first with magnesium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4979dccbfd9749eab09995a31b0c5947
Source dataset
uspto-grants-1983_02
Patent number
US04371605

Reaction notes

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