Formaldehyde → 4-fluoro-2-methylamino-benzoic Acid
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[CH2:12]=O.[H][H]>[Pd].C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:11][CH3:12])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 4-fluoroanthranilic acid (2 g), aqueous formaldehyde (37-40% w/v; 6.5 ml) and palladium on charcoal (1 g of 5%) in acetic acid (70 ml) was hydrogenated over 18 hours during which 570 ml hydrogen was taken up. The mixture was filtered, evaporated under reduced pressure and the residue recrystallised from toluene to give 4-fluoro-N-methylanthranilic acid, m.p. 180°-181°. (Compound 7)
Workup
- filtrationThe mixture was filtered
- customevaporated under reduced pressure
- customthe residue recrystallised from toluene
Sources & evidence
- ORD record
- ord-1e368b4ec70a43808068c05308364994
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05093364
Reaction notes
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