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

HRID 2098393ノート

反応式

HRID 2098393 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  1. customThe resulting precipitated yellow solid
  2. filtrationwas collected by filtration
  3. washwashed with IPA
  4. customdried in vacuo The filtrate
  5. customwas 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

出典と根拠

ORDレコード
ord-ce2b3694e30e44c3867e4942a4232073
出典データセット
uspto-grants-2013_05
特許番号
US08450506B2

反応ノート

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