HCID 25248372, compound → HCID 19627217, compound

HRID 526755Notes

Reaction equation

HRID 526755 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H][H]>[Pd].CO>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 25248372HCID 25248372, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19627217HCID 19627217, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-fluoro-4-nitro-1-phenoxybenzene (3.2 g, 13.72 mmol, 1.00 equiv) and methanol (100 mL) was added 10% palladium on carbon (0.5 g) catalyst. The reaction mixture was stirred under 1 atmosphere of hydrogen at room temperature for 4 h. The catalyst was removed by filtration. The filtrate was concentrated under vacuum to give 2.65 g (95%) of 3-fluoro-4-phenoxybenzenamine as an off-white solid. 1H-NMR (300 MHz, CDCl3): δ 7.29-7.19 (m, 2H), 7.03-6.83 (m, 4H), 6.52-6.36 (m, 2H), 3.63 (s, 2H) ppm.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-efb022182d6d42d18296e141340cf54a
Source dataset
uspto-grants-2016_05
Patent number
US09346761B2

Reaction notes

Loading…