HCID 9796071, compound → HCID 18619998, compound

HRID 49315Notes

Reaction equation

HRID 49315 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([CH2:19][N:20]=[N+]=[N-])[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][CH:8]=1)#[N:2].[H][H]>C(O)C.C(=O)([O-])[O-].[Ba+2].[Pd+2].C(=O)([O-])[O-]>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([CH2:19][NH2:20])[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 9796071HCID 9796071, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18619998HCID 18619998, compound

Reagents, catalysts & solvents 2

HCID 16211661HCID 16211661, compoundCatalystHCID 702EthanolSolvent

Procedure

The Methyl 3-(3-cyanophenyl)-5-(azidomethyl)benzoate obtained as above was put in a flask, dissolved in 66 mL of ethanol, and after 1.1 g of palladium-barium carbonate was added, the air in flask was displaced with hydrogen. Stirring was continued at room temperature for 6 hours, the catalyst was subjected to celite-filteration, and the filtrate was concentrated and purified with silica gel chromatography to produce 794 mg of the title compound (Yield of the two steps: 90%).

Workup

  1. customas above was put in a flask
  2. concentrationthe filtrate was concentrated
  3. custompurified with silica gel chromatography

Sources & evidence

ORD record
ord-a6ef6f7eda4a461bb53e1b0fad0b8743
Source dataset
uspto-grants-2004_03
Patent number
US06706745B1

Reaction notes

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