5-(7-Azabicyclo[2.2.1]heptan-7-yl)-2-nitrobenzonitrile → 2-Amino-5-(7-azabicyclo[2.2.1]heptan-7-yl)benzonitrile

HRID 1908221Notes

Reaction equation

HRID 1908221 reaction equation
[CH:1]12[N:7]([C:8]3[CH:9]=[CH:10][C:11]([N+:16]([O-])=O)=[C:12]([CH:15]=3)[C:13]#[N:14])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2>[Pd]>[NH2:16][C:11]1[CH:10]=[CH:9][C:8]([N:7]2[CH:1]3[CH2:6][CH2:5][CH:4]2[CH2:3][CH2:2]3)=[CH:15][C:12]=1[C:13]#[N:14]

Participants

3

Reactant 1

HCID 575168455-(7-Azabicyclo[2.2.1]heptan-7-yl)-2-nitrobenzonitrile

Product 1

HCID 575168442-Amino-5-(7-azabicyclo[2.2.1]heptan-7-yl)benzonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A flask charged with 5-(7-azabicyclo[2.2.1]heptan-7-yl)-2-nitrobenzonitrile 22 (205 mg, 0.8427 mmol) and 10% Pd/C (41 mg, 0.39 mmol) was flushed with nitrogen and then evacuated under vacuum. Methanol (4 mL) was added under nitrogen atmosphere and the flask was fitted with a hydrogen balloon. After stirring for 15 min, the Pd/C was removed by filtration and solvent was removed under reduced pressure to provide 2-amino-5-(7-azabicyclo[2.2.1]heptan-7-yl)benzonitrile 23 (170 mg, 95% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 7.02 (dd, J=2.8, 9.0 Hz, 1H), 6.87 (d, J=2.7 Hz, 1H), 6.68 (d, J=9.0 Hz, 1H), 5.36 (s, 2H), 4.09 (s, 2H), 1.59 (d, J=6.8 Hz, 4H), 1.34 (d, J=6.8 Hz, 4H).

Workup

  1. customwas flushed with nitrogen
  2. customevacuated under vacuum
  3. additionMethanol (4 mL) was added under nitrogen atmosphere
  4. customthe flask was fitted with a hydrogen balloon
  5. customthe Pd/C was removed by filtration and solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-e081857308864126b37392915333b50c
Source dataset
uspto-grants-2013_12
Patent number
US08598205B2

Reaction notes

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