2-Fluoro-4-nitrobenzonitrile → 4-(Aminomethyl)-3-fluoroaniline

HRID 1438137Notes

Reaction equation

HRID 1438137 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]>CO.Cl.[Pd]>[NH2:5][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:2]=1[F:1]

Participants

5

Reactant 1

HCID 27590482-Fluoro-4-nitrobenzonitrile

Product 1

HCID 442031254-(Aminomethyl)-3-fluoroanilineYield 190.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 2-fluoro-4-nitrobenzonitrile (0.541 g, 2.43 mmol) in methanol (20 mL) and 6N hydrochloric acid (3 mL) was hydrogenated (55 psi) over 10% palladium on carbon (164 mg) for 22 h. The reaction mixture was filtered and concentrated in vacuo to afford 77A (0.65 g, 100%). 1H NMR (400 MHz, CD3OD) δ 4.23 (s, 2H), 7.29 (d, J=8.79 Hz, 2H), 7.68 (t, J=7.91 Hz, 1H).

Workup

  1. customfor 22 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c29542fe78c5444db7f11ad1856344cc
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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