Water → HCID 85272219, compound

HRID 1451106Notes

Reaction equation

HRID 1451106 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.Cl.[NH2:17][OH:18].O>C(O)C>[OH:18][N:17]=[CH:1][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 10846077METHYL 3-FORMYL-5-NITROBENZOATE

Product 1

HCID 85272219HCID 85272219, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 3-formyl-5-nitrobenzoate (0.418 g, 2.0 mmol), hydroxylamine hydrochloride (0.209 g, 3.0 mmol) in ethanol (5.0 mL) was heated at reflux for 2 h. On cooling, the mixture was poured into water and the precipitate collected by filtration. The cake was recrystallized from ethyl acetate-hexane and dried to give 0.22 g (49%) of methyl 3-[(N-hydroxylimino)methyl]-5-nitrobenzoate as an off-white solid, mp 144°-145° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperatureOn cooling
  4. filtrationthe precipitate collected by filtration
  5. customThe cake was recrystallized from ethyl acetate-hexane
  6. customdried

Sources & evidence

ORD record
ord-5153612bb1894f96b5f356bd0953af5c
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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