Formaldehyde → Methyl N-methylanthranilate
Reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH2:12]=O.[H][H]>[Pt]=O.C(O)C>[CH3:12][NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([O:10][CH3:11])=[O:9]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
In a 250 mL Parr shaking glass pressure reactor was placed methyl anthranilate (37.75 g, 0.25 mol), 95% ethanol (80 mL), and platinum oxide (0.5 g). To this cooled mixture at 5° C. was added 37% formaldehyde solution (20 mL, 0.25 mol). This resultant mixture was immediately hydrogenated at room temperature at a hydrogen pressure of 50 psig. Over a period of 5 hours no hydrogen uptake was observed. The dimer, however, did form as evidenced by a solid precipitate, but no methyl N-methylanthranilate was produced.
Sources & evidence
- ORD record
- ord-b152cbb3229e4e9ca7ba69e6dbe50195
- Source dataset
- uspto-grants-1986_12
- Patent number
- US04633009
Reaction notes
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