Methanol → HCID 16110241, compound

HRID 902167Notes

Reaction equation

HRID 902167 reaction equation
[CH2:1]([NH:5][C:6](=[O:21])[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[N+:18]([O-])=O)=[O:8])[CH2:2][CH2:3][CH3:4].CO>[Pd].CC(C)=O>[NH2:18][C:11]1[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=1[NH:9][C:7](=[O:8])[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:21]

Participants

5

Reactant 2

HCID 887MethanolHCID 16110263HCID 16110263, compound

Product 1

HCID 16110241HCID 16110241, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 27.0 g (91 mmol) of N-Butyl-N′-(4-methoxy-2-nitro-phenyl) oxalamide, 1200 ml of methanol and 7.3 g of 5% Pd/C catalyst is hydrogenated from 3 h. To the reaction mixture is added 600 ml of acetone. The catalyst is filtered off, washed with acetone, the filtrate is concentrated and the residue si crystallized with diethyl ether to yield 21.8 g (90.1%) of the titled compound. Mp.: 180-181° C. (diethyl ether).

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with acetone
  3. concentrationthe filtrate is concentrated
  4. customthe residue si crystallized with diethyl ether

Sources & evidence

ORD record
ord-bf0befc3b8234577a224521021c8e553
Source dataset
uspto-grants-2008_04
Patent number
US07365083B2

Reaction notes

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