4-Nitrobenzaldehyde → p-Nitrobenzaldoxime

HRID 1371825Notes

Reaction equation

HRID 1371825 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].CO.Cl.[NH2:15][OH:16].C(=O)([O-])[O-].[Na+].[Na+]>O>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[N:15][OH:16])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 887MethanolHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 96339p-NitrobenzaldoximeYield 90.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

4-Nitrobenzaldehyde (40 g, 264.49 mmol) was added to MeOH (100 ml) followed by hydroxylamine hydrochloride (22.9 g, 330.9 mmol) in H2O (100 ml). The solution was then cooled to 0° C. Sodium carbonate (16.9 g, 159.5 mmol) in H2O (100 ml) was added and the reaction was allowed to stir overnight. The MeOH was removed under vacuum and then H2O (400 ml) was added. The precipitate was filtered and dried under vacuum to yield the product (39.65 g, 238.68 mmol).

Workup

  1. customThe MeOH was removed under vacuum
  2. additionH2O (400 ml) was added
  3. filtrationThe precipitate was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ec7fc1ca8c9640918ac06ee54eb61d91
Source dataset
uspto-grants-2007_01
Patent number
US07157482B2

Reaction notes

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