2-(Azidomethyl)-4-methoxybenzonitrile → HCID 22464511, compound

HRID 1935439Notes

Reaction equation

HRID 1935439 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:4]=1[CH2:5][N:6]=[N+]=[N-])#[N:2]>[Pd].C(OCC)(=O)C>[C:1]([C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:4]=1[CH2:5][NH2:6])#[N:2]

Participants

4

Reactant 1

HCID 224645382-(Azidomethyl)-4-methoxybenzonitrile

Product 1

HCID 22464511HCID 22464511, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-cyano-5-methoxybenzyl azide (1 g, 5.3 mmol) and 10% palladium on carbon (500 mg) in ethyl acetate (30 ml) was stirred at room temperature under an atmosphere of hydrogen for 1 h. The catalyst was removed by filtration through a bed of Celite and the filtrate concentrated to yield the product as an orange oil: 1H NMR (CDCl3) δ7.56 (d, J=8.5 Hz, 1H), 7.07 (d, J=2.5 Hz, 1H), 6.82 (dd, J=2.5, 8.5 Hz, 1H), 4.05 (br s, 2H), 3.87 (s, 3H).

Workup

  1. customThe catalyst was removed by filtration through a bed of Celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-cbf7407eddb34dcab2bfc77e88c50153
Source dataset
uspto-grants-2002_05
Patent number
US06387911B1

Reaction notes

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