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

HRID 1096583노트

반응식

HRID 1096583 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a9b417c3145243cc920a9153851ca9ff
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138357B2

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