HCID 59452984, compound → HCID 23348947, compound

HRID 419353Notes

Reaction equation

HRID 419353 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([CH2:11][CH:12]=[CH2:13])[CH:3]=1>CO.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH2:11][CH2:12][CH3:13])[CH:3]=1

Participants

4

Reactant 1

HCID 59452984HCID 59452984, compound

Product 1

HCID 23348947HCID 23348947, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To 4-fluoro-1-nitro-2-(2-propen-1-yl)benzene (9.0 g, 50 mmol) in MeOH (100 mL) was added palladium hydroxide on carbon (2 g). The reaction mixture was stirred under H2 (50 psi) at rt overnight. The solution was filtered and concentrated to provide the title compound of step C (7.4 g, 48.3 mmol, 97%). 1H NMR (400 MHz, CDCl3) δ ppm 1.10 (t, J=7.5 Hz, 3H), 1.60-1.70 (m, 2H), 2.45 (t, J=7.2 Hz, 2H), 6.55-6.65 (m, 1H), 6.67-6.81 (m, 2H).

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7df700b8866548d5ada54bbacfc0aa6a
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

Loading…