Potassium Hydroxide → N-hydroxy-2-methoxy-5-nitrobenzamide

HRID 1096578Notes

Reaction equation

HRID 1096578 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:4]=1[C:5](OC)=[O:6].Cl.[NH2:17][OH:18].[OH-].[K+]>CO>[OH:18][NH:17][C:5](=[O:6])[C:4]1[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 7020925Benzoic acid, 2-methoxy-5-nitro-, methyl ester

Product 1

HCID 57687781N-hydroxy-2-methoxy-5-nitrobenzamideYield 101.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 2-methoxy-5-nitrobenzoate (10 g, 47.39 mmol) and hydroxylamine hydrochloride (13.17 g, 189.56 mmol) were taken up in MeOH (100 ml) and a solution of KOH (13.27 g, 236.95 mmol) in MeOH (55 ml) was added carefully. Note—an exothermic reaction was observed; solids initially dissolved, then a solid precipitated out of solution. TLC (run in EtOAc) of an acid washed aliquot showed a trace of the starting benzoate and a new product. H2O (100 ml) was added and any undissolved solid collected by filtration off, washed with isopropyl alcohol (IPA) and dried in vacuo to give 10.23 g (>100%) of N-hydroxy-2-methoxy-5-nitrobenzamide as a white solid.

Workup

  1. customreaction
  2. dissolutionsolids initially dissolved
  3. customa solid precipitated out of solution
  4. washTLC (run in EtOAc) of an acid washed aliquot
  5. additionH2O (100 ml) was added
  6. filtrationany undissolved solid collected by filtration off,
  7. washwashed with isopropyl alcohol (IPA)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-2c9d7080a74d4c1284c43ea4333419b8
Source dataset
uspto-grants-2012_03
Patent number
US08138357B2

Reaction notes

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