2-Fluoro-5-nitrobenzonitrile → 5-Amino-2-fluorobenzonitrile

HRID 1768113Notes

Reaction equation

HRID 1768113 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:3]=1[C:4]#[N:5]>C(O)C.[Pd]>[NH2:10][C:7]1[CH:8]=[CH:9][C:2]([F:1])=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

4

Reactant 1

HCID 5194172-Fluoro-5-nitrobenzonitrile

Product 1

HCID 27376735-Amino-2-fluorobenzonitrileYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 2-fluoro-5-nitrobenzonitrile (5.20 g) in ethanol (150 mL) was added 5% Pd/C (1.00 g). The reaction was placed on a hydrogenator (50 psi) for 10 minutes. The reaction mixture was filtered through celite and the filtrate evaporated to give 4.25 g of 5-amino-2-fluorobenzonitrile. 1H NMR (CDCl3) δ 3.75 (bs, 2H, NH2), 6.83 (m, 2H, aromatic H), 6.99 (m, 1H, aromatic H). GC mass spectrum z (rel. intensity) 137 (M+H, 100).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-3c22e66c76564ac8b75cf0adca2fce96
Source dataset
uspto-grants-2007_06
Patent number
US07235575B2

Reaction notes

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