Hydroxylamine → 2-Ethoxy-N-hydroxy-5-nitrobenzamide

HRID 1096583Notes

Reaction equation

HRID 1096583 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:5]=1[C:6](OC)=[O:7])[CH3:2].[NH2:17][OH:18]>CO>[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:5]=1[C:6]([NH:17][OH:18])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 43449037Methyl 2-ethoxy-5-nitrobenzoate

Product 1

HCID 576877782-Ethoxy-N-hydroxy-5-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-ethoxy-5-nitrobenzoate (6.099 g, 26.99 mmol) and 50% wt/v aqueous hydroxylamine (40 ml) were taken up in MeOH (100 ml) and stirred at RT overnight. The resulting precipitated yellow solid was collected by filtration, washed with IPA and dried in vacuo. The filtrate was evaporated in vacuo and the residue was triturated with IPA (25 ml). The solid that didn't dissolve was filtered off, washed with a minimum quantity of IPA and dried in vacuo. The two crops of solid were suspended in H2O (300 ml) and the pH was lowered to 2 by careful addition of concentrated HCl. The solid was filtered off, washed with MTBE and dried in vacuo to give 3.9 g of crude 2-ethoxy-5-nitro-N-hydroxybenzamide. The IPA mother liquors from above were combined with the crude 2-ethoxy-5-nitro-N-hydroxybenzamide and evaporated in vacuo. The residue was triturated with CH2Cl2 (25 ml) and the solid was filtered off and dried in vacuo to give 2-ethoxy-5-nitro-N-hydroxybenzamide (2.39 g, 39%) as a yellow solid.

Workup

  1. customThe resulting precipitated yellow solid
  2. filtrationwas collected by filtration
  3. washwashed with IPA
  4. customdried in vacuo
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was triturated with IPA (25 ml)
  7. dissolutionThe solid that didn't dissolve
  8. filtrationwas filtered off
  9. washwashed with a minimum quantity of IPA
  10. customdried in vacuo
  11. additionthe pH was lowered to 2 by careful addition of concentrated HCl
  12. filtrationThe solid was filtered off
  13. washwashed with MTBE
  14. customdried in vacuo

Sources & evidence

ORD record
ord-a9b417c3145243cc920a9153851ca9ff
Source dataset
uspto-grants-2012_03
Patent number
US08138357B2

Reaction notes

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