Hydrochloric Acid → Methyl 4-(2-aminoacetyl)benzoate hydrochloride

HRID 606587Notes

Reaction equation

HRID 606587 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:15])[CH2:11][N:12]=[N+]=[N-])=[CH:6][CH:5]=1.[ClH:17].[H][H]>CO.[Pd]>[ClH:17].[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:15])[CH2:11][NH2:12])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 71414038Methyl 4-(azidoacetyl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 67046619Methyl 4-(2-aminoacetyl)benzoate hydrochlorideYield 86.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4(2-Azido-acetyl)-benzoic acid methyl ester (6.53 mmol) was suspended in methanol (30 ml) and aqueous hydrochloric acid (6.53 mmol, 1M) was added. A catalytic amount of palladium on carbon (10% wt) was added and the reaction stirred over an atmosphere of hydrogen for 3 h. The reaction was filtered and the solvent removed in vacuo to give the title compound (1.3 g) as a yellow solid m/z=194 in MS ES+, which was used in the next step without purification.

Workup

  1. filtrationThe reaction was filtered
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1ac924bf69a04ff489dbdc0220747160
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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