Hydrochloric Acid → HCID 18476067, compound

HRID 2187623Notes

Reaction equation

HRID 2187623 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])=[N+]=[N-].Cl>[Pd].CO>[NH2:1][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18476026HCID 18476026, compound

Product 1

HCID 18476067HCID 18476067, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 5-azidomethyl-2-(4-fluorobenzyl)benzoate (3.23 g), 10% palladium on carbon (0.5 g), 1M. ethereal HCl (20 ml) and methanol (100 ml) was stirred under an atmosphere of hydrogen for 6 hours. The catalyst was filtered off and the filtrate was evaporated to dryness. The residue was treated with saturated aqueous sodium bicarbonate (100 ml) and extracted with ethyl acetate. The solution obtained was dried and evaporated to dryness to give methyl 5-aminomethyl-2-(4-fluorobenzyl)benzoate as a colourless gum (2.7 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated to dryness
  3. additionThe residue was treated with saturated aqueous sodium bicarbonate (100 ml)
  4. extractionextracted with ethyl acetate
  5. customThe solution obtained
  6. customwas dried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-1779d89e6ee24915af75e805cae612a7
Source dataset
uspto-grants-2002_06
Patent number
US06410539B1

Reaction notes

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