Methanol → HCID 16110241, compound

HRID 896440Notes

Reaction equation

HRID 896440 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-96a78199d1434b8eb2a591ac9aa02f49
Source dataset
uspto-grants-2005_07
Patent number
US06919355B2

Reaction notes

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