HCID 16110263, compound → HCID 16110241, compound

HRID 900799Notes

Reaction equation

HRID 900799 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]>[Pd].CO>[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

4

Reactant 1

HCID 16110263HCID 16110263, compound

Product 1

HCID 16110241HCID 16110241, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 27.0 g (91 mmol) of N-butyl-N′-(4-methoxy-2-nitrophenyl)-oxalamide, 1200 ml of methanol and 7.3 g of 10% Pd/C catalyst is hydogenated for 3 h. The catalyst is filtered off, washed with aceton, the filtrate is concentrated and the residue is treated with 100 ml of diethyl ether. The obtained product is filtered, washed with diethyl ether and dried to yield 21.8 g (90%) of the title compound. Mp.: 180-181° C. (diethyl ether).

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with aceton
  3. concentrationthe filtrate is concentrated
  4. additionthe residue is treated with 100 ml of diethyl ether
  5. filtrationThe obtained product is filtered
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-5900825e419b45b982d50c517266a84b
Source dataset
uspto-grants-2008_04
Patent number
US07361670B2

Reaction notes

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