Formaldehyde → 4-fluoro-2-methylamino-benzoic Acid

HRID 2371441Notes

Reaction equation

HRID 2371441 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

HCID 712FormaldehydeHCID 27249674-Fluoroanthranilic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 104420994-fluoro-2-methylamino-benzoic Acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

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

  1. filtrationThe mixture was filtered
  2. customevaporated under reduced pressure
  3. 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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