Ethyl Acetate → HCID 22285308, compound

HRID 586270Notes

Reaction equation

HRID 586270 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]1[N:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]#[N:14].C(OCC)(=O)C.[H][H]>C(O)C.[Pt](=O)=O>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:11]2[N:18]=[CH:17][CH:16]=[CH:15][C:12]=2[C:13]#[N:14])[CH:4]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 22285317HCID 22285317, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22285308HCID 22285308, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(2-fluoro-5-nitrophenyl)nicotinonitrile (1.2 g, 4.9 mmol) and platinum(IV) oxide in ethanol (50 ml) with ethyl acetate (50 ml) was reduced under 40 psi hydrogen for 30 minutes then filtered and the solvent removed to give an orange oil. Purification by chromatography (silica gel, 1% MeOH/CH2Cl2) gave 2-(5-amino-2-fluorophenyl)-nicotinonitrile as an orange oil: 1H NMR (360 MHz, CDCl3) δ 8.88 (1H, dd, J 2, 5 Hz), 8.07 (1H, dd, J 2, 8 Hz), 7.42 (1H, dd, J 5, 8 Hz), 7.04 (1H, t, J 9 Hz), 6.85 (1H, dd, J 3, 6 Hz), 6.76-6.81 (1H, m); MS (ES+) m/z 214 [M+H]+.

Workup

  1. filtrationthen filtered
  2. customthe solvent removed
  3. customto give an orange oil
  4. customPurification by chromatography (silica gel, 1% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-5a97e84012974ec49559ba29d3374ebe
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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