4-Fluoroaniline → HCID 59745253, compound

HRID 2196866Notes

Reaction equation

HRID 2196866 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[NH:5][C:6]1[C:7]([N+:16]([O-:18])=[O:17])=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=O)[CH2:10][CH2:9]2)[CH3:2].[F:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1.[B][B][B][B][B][B][B][B][B][B]>CO>[CH2:1]([O:3][C:4](=[O:19])[NH:5][C:6]1[C:7]([N+:16]([O-:18])=[O:17])=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH:11]([NH:25][C:24]1[CH:26]=[CH:27][C:21]([F:20])=[CH:22][CH:23]=1)[CH2:10][CH2:9]2)[CH3:2]

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 59745249HCID 59745249, compoundHCID 178419135HCID 178419135, compound

Product 1

HCID 59745253HCID 59745253, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (4-nitro-1-oxo-indan-5-yl)-carbamic acid ethyl ester (0.47 g, 1.8 mmol), 4-fluoroaniline (0.24 g, 2.2 mmol), and decaborane (200 mg) in 20 ml of anhydrous methanol was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was purified by chromatography using a mixture of hexane/EtOAc (5:1) as eluant to give a pure product (0.54 g, 83%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by chromatography
  3. additiona mixture of hexane/EtOAc (5:1) as eluant

Sources & evidence

ORD record
ord-b11127c79e5243a7a3745476a6ffc8fc
Source dataset
uspto-grants-2012_12
Patent number
US08338487B2

Reaction notes

Loading…