HCID 85272219, compound → HCID 85247288, compound

HRID 1451107Notes

Reaction equation

HRID 1451107 reaction equation
[OH:1][N:2]=[CH:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N+:14]([O-])=O)[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]>C(O)C.[Pt]=O>[NH2:14][C:12]1[CH:11]=[C:6]([CH:5]=[C:4]([CH:3]=[N:2][OH:1])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 85272219HCID 85272219, compound

Product 1

HCID 85247288HCID 85247288, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of methyl 3-[(N-hydroxylimino)methyl]-5-nitrobenzoate (2.0 g, 0.009 mol) in ethanol (150 mL) was hydrogenated in the presence of platinum oxide (0.25 g) at 30 psi for 0.5 h. The catalyst was removed by filtration through Celite and the filtrate was concentrated. The residue was recrystallized from ethyl acetate-hexane to give 1.1 g (64%) of methyl 3-amino-5-[(N-hydroxylimino)methyl]benzoate as an off-white solid, mp 160°-162° C.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-72bab7d9f7594470b501cc4b41296762
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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