Hydroxylamine → Methyl 5-(N'-hydroxycarbamimidoyl)-2,4-dimethylbenzoate

HRID 541192Notes

Reaction equation

HRID 541192 reaction equation
[C:1]([C:3]1[C:4]([CH3:14])=[CH:5][C:6]([CH3:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].[NH2:15][OH:16]>CCO>[OH:16][N:15]=[C:1]([C:3]1[C:4]([CH3:14])=[CH:5][C:6]([CH3:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])[NH2:2]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 68288737Methyl 5-cyano-2,4-dimethylbenzoate2×

Product 1

HCID 86672521Methyl 5-(N'-hydroxycarbamimidoyl)-2,4-dimethylbenzoateYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 5-cyano-2,4-dimethylbenzoate (compound 2.3, 6 g, 28.54 mmol, 1.00 equiv, 90%) and NH2OH (10 mL, 5.00 equiv, 50% in water) in EtOH (20 mL) was stirred at 100° C. in an oil bath. After 2 h, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with 100 mL of ethyl acetate, washed with 2×20 mL of brine, dried (Na2SO4), and concentrated under reduced pressure to yield 4.66 g (66%) of the title compound as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with 100 mL of ethyl acetate
  3. washwashed with 2×20 mL of brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-acb1e0d640bd43b2bb246f1df5bbbf6a
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

Loading…