1-(2-(4-Fluorophenyl)acetyl)-3-(4-nitrophenyl)urea → 1-(4-Aminophenyl)-3-(2-(4-fluorophenyl)acetyl)urea

HRID 2117133Notes

Reaction equation

HRID 2117133 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)=[O:13])=[O:10])=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:12]([NH:11][C:9](=[O:10])[CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:13])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 210814671-(2-(4-Fluorophenyl)acetyl)-3-(4-nitrophenyl)ureaHCID 178418361HCID 178418361, compound

Product 1

HCID 210815251-(4-Aminophenyl)-3-(2-(4-fluorophenyl)acetyl)ureaYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2-(4-fluorophenyl)acetyl)-3-(4-nitrophenyl)urea (200 mg, 0.63 mmol) in ethyl acetate (10 mL) was added 10% palladium on carbon (15 mg) and the flask was filled with hydrogen using a balloon. The mixture was stirred for 18 h, filtered and the catalyst was washed with ethyl acetate. The filtrate was concentrated in vacuo to give a solid which was was triturated with small amount of ether and dried in vacuo to obtain the desired compound (180 mg) as pale yellow solid. MS(ESI+) m/z 287.4 (M+H)+.

Workup

  1. filtrationfiltered
  2. washthe catalyst was washed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give a solid which
  5. customwas was triturated with small amount of ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-4cabb13eb7334d358df2c56f5cf20da4
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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