1-(4-Methoxy-2-nitrophenyl)-3-cyclopentylurea → 1-(2-Amino-4-methoxyphenyl)-3-cyclopentylurea

HRID 1901054Notes

Reaction equation

HRID 1901054 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:11])=[C:5]([N+:18]([O-])=O)[CH:4]=1>C(O)C.[Pd]>[NH2:18][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[NH:9][C:10]([NH:12][CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11]

Participants

4

Reactant 1

HCID 233700901-(4-Methoxy-2-nitrophenyl)-3-cyclopentylurea

Product 1

HCID 233701321-(2-Amino-4-methoxyphenyl)-3-cyclopentylureaYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 1-(4-methoxy-2-nitrophenyl)-3-cyclopentylurea (0.96 g) in ethanol (15 ml) was added a catalytic amount of 10% palladium/carbon to carry out catalytic reduction at a pressure of 1-2.5 arms at room temperature for 2 hrs. The catalyst was filtered off, the solvent was distilled off and crystallization of the residue from benzene and hexane afforded 1-(2-amino-4-methoxyphenyl)-3-cyclopentylurea (0.79 g, 93%).

Workup

  1. customat room temperature
  2. customfor 2 hrs
  3. filtrationThe catalyst was filtered off
  4. distillationthe solvent was distilled off
  5. customcrystallization of the residue from benzene and hexane

Sources & evidence

ORD record
ord-db9599b6283444d1944b30157dab1e0b
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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