Pyridine → HCID 67105969, compound

HRID 2244153Notes

Reaction equation

HRID 2244153 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]#[N:16])[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.N1C=CC=CC=1>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]#[N:16])[CH:10]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 1049PyridineHCID 23373333HCID 23373333, compound

Product 1

HCID 67105969HCID 67105969, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

10% Degussa Pd on carbon (40 mg, 0.38 mmol) was flushed with nitrogen then diluted in ethanol (5 mL). 4-(4-Nitro-benzyl)-pyridine-2-carbonitrile (250 mg, 1.05 mmol) in ethanol (5 mL) and pyridine (42 mg, 0.52 mmol) was subsequently added, and the mixture was flushed again with nitrogen prior to placing a hydrogen balloon on the flask. The mixture was stirred at rt overnight then filtered through Celite® and concentrated. The residue was dissolved in ethyl acetate and filtered through a silica gel plug, eluting with 50-100% ethyl acetate in hexanes, to give 4-(4-amino-benzyl)-pyridine-2-carbonitrile (134 mg, 61%). 1H NMR (CHCl3-d) δ 8.55 (d, J=5.2 Hz, 1H), 7.46 (s, 1H), 7.30 (d, J=4.8 Hz, 1H), 6.93 (d, J=8.3 Hz, 2H), 6.66 (d, J=8.2 Hz, 2H), 3.91 (s, 2H).

Workup

  1. customthe mixture was flushed again with nitrogen
  2. filtrationthen filtered through Celite®
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. filtrationfiltered through a silica gel plug
  6. washeluting with 50-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-eb60b03f08c94776b5a000a868441862
Source dataset
uspto-grants-2010_03
Patent number
US07678804B2

Reaction notes

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