Methyl 4-(azidomethyl)-3-methoxybenzoate → HCID 57445597, compound

HRID 2355274Notes

Reaction equation

HRID 2355274 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]=[N+]=[N-])=[C:6]([O:14][CH3:15])[CH:5]=1>[Pd].C(O)C>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH2:11])=[C:6]([O:14][CH3:15])[CH:5]=1

Participants

4

Reactant 1

HCID 57445596Methyl 4-(azidomethyl)-3-methoxybenzoate

Product 1

HCID 57445597HCID 57445597, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrogenate a mixture of 4-azidomethyl-3-methoxy-benzoic acid methyl ester (4.1 g, 18.5 mmol) and palladium on carbon (4.9 g, 4.63 mmol) in ethanol (200 mL) under a hydrogen atmosphere at 345 KPa for 24 hrs at room temperature. Filter the reaction mixture through diatomaceous earth and concentrate the filtrate to provide the crude title compound (2.9 g, 14.9 mmol). MS (m/z): 196 (M+1). Use it as is in next step.

Workup

  1. filtrationFilter the reaction mixture through diatomaceous earth
  2. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-e89239be72a3416f90f768bb5e0adf7a
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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