4-Azidomethyl-2-(2-methylphenyl)benzoic acid methyl ester → 4-Aminomethyl-2-(2-methylphenyl)benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]=[N+]=[N-])=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]>CO.Cl>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH2:11])=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]Participants
4
Procedure
To a flask at ambient temperature under N2 containing 10% palladium on carbon catalyst (1.0 g) was added a solution of 4-azidomethyl-2-(2-methylphenyl)benzoic acid methyl ester (5.00 g, 17.8 mmol), prepared as in Example 1191A, in MeOH (75 mL). Two drops of conc. HCl added, and reaction stirred vigorously overnight under an atmosphere of H2. Catalyst filtered off through celite and washed with MeOH. Filtrate concentrated in vacuo, and residue taken up in an aqueous 4N NaOH solution. Aqueous solution extracted with CHCl3 (3×), and extracts dried with Na2SO4, filtered, and concentrated in vacuo to afford the desired product (1.37 g, 30%). m/e (DCI) 256 (MH+)
Workup
- additionTo a flask at ambient temperature under N2 containing 10% palladium on carbon catalyst (1.0 g) was added
- customreaction
- filtrationCatalyst filtered off through celite
- washwashed with MeOH
- concentrationFiltrate concentrated in vacuo, and residue
- extractionAqueous solution extracted with CHCl3 (3×), and extracts
- dry with materialdried with Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-0f8b198dd3d34025bdbea41c1ea81023
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06310095B1
Reaction notes
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