Tetrahydrofuran → Ethyl {[4-amino-2-(aminocarbonyl)phenyl]amino}(oxo)acetate

HRID 606491Notes

Reaction equation

HRID 606491 reaction equation
[NH2:1][C:2]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[NH:13][C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:3].C1COCC1>[C].[Pd].C(O)C>[NH2:10][C:8]1[CH:7]=[CH:6][C:5]([NH:13][C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:4]([C:2]([NH2:1])=[O:3])[CH:9]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 12264866Ethyl {[2-(aminocarbonyl)-4-nitrophenyl]amino}(oxo)acetate

Product 1

HCID 66769061Ethyl {[4-amino-2-(aminocarbonyl)phenyl]amino}(oxo)acetateYield 96%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl {[2-(aminocarbonyl)-4-nitrophenyl]amino}(oxo)acetate (2.292 g) in a mixed solvent of THF (100 mL)-ethanol (50 mL) was added 10% palladium carbon (405 mg), and the mixture was subjected to catalytic reduction under hydrogen atmosphere at room temperature for 8 hr. The catalyst was filtered off, and the filtrate was concentrated. The obtained crude crystals were washed with diisopropyl ether to give ethyl {[4-amino-2-(aminocarbonyl)phenyl]amino}(oxo)acetate (1.96 g, 96%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe obtained crude crystals
  4. washwere washed with diisopropyl ether

Sources & evidence

ORD record
ord-380dd0ea75634de79066fd93a3dd64dc
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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