1-(4-Fluoro-2-nitrophenyl)-3-heptylurea → 1-(2-Amino-4-fluorophenyl)-3-heptylurea

HRID 1901056Notes

Reaction equation

HRID 1901056 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:10])=[C:4]([N+:19]([O-])=O)[CH:3]=1>C(O)C.[Pd]>[NH2:19][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[NH:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:10]

Participants

4

Reactant 1

HCID 233700951-(4-Fluoro-2-nitrophenyl)-3-heptylurea

Product 1

HCID 233700761-(2-Amino-4-fluorophenyl)-3-heptylureaYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 1-(4-fluoro-2-nitrophenyl)-3-heptylurea (1.49 g) in ethanol (10 ml) was added a catalytic amount of 10% palladium/carbon to perform catalytic reduction at a pressure of 1-2.5 atms at room temperature for 5 hrs. The catalyst was filtered off, and the solvent was distilled off. Crystallization of the residue from hexane gave 1-(2-amino-4-fluorophenyl)-3-heptylurea (1.26 g, 95%).

Workup

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

Sources & evidence

ORD record
ord-5e7f99d1968b46118e9426aa54d4a903
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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