Methanol → 5-Amino-2-ethoxy-N-hydroxybenzamide

HRID 1096584Notes

Reaction equation

HRID 1096584 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:5]=1[C:6]([NH:8][OH:9])=[O:7])[CH3:2].CO>CCO.[Pd]>[NH2:14][C:11]1[CH:12]=[CH:13][C:4]([O:3][CH2:1][CH3:2])=[C:5]([CH:10]=1)[C:6]([NH:8][OH:9])=[O:7]

Participants

5

Reactant 2

HCID 887MethanolHCID 576877782-Ethoxy-N-hydroxy-5-nitrobenzamide

Product 1

HCID 160422955-Amino-2-ethoxy-N-hydroxybenzamideYield 726%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

2-Ethoxy-5-nitro-N-hydroxybenzamide (2.39 g, 1.06 mmol) was suspended in EtOH (50 ml) and 10% Pd on carbon (wet basis) (240 mg) was added. The mixture was hydrogenated at 50 psi for 1.5 hrs. MeOH (50 ml) was added and the mixture was filtered through celite. The volatiles were removed in vacuo and the residue was taken up in IPA (50 ml). The mixture was heated at 60° C. for 0.5 hr then stood at RT overnight. The precipitated solid was collected by filtration, washed with MTBE and dried in vacuo to give 1.51 g of 5-amino-2-ethoxy-N-hydroxybenzamide (73%) as an off-white solid.

Workup

  1. filtrationthe mixture was filtered through celite
  2. customThe volatiles were removed in vacuo
  3. waitthen stood at RT overnight
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with MTBE
  6. customdried in vacuo

Sources & evidence

ORD record
ord-cc2e67bf8d8244cd868a718149d2cf41
Source dataset
uspto-grants-2012_03
Patent number
US08138357B2

Reaction notes

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