Anthranilic Acid → N-Methylanthranilic acid

HRID 1583248Notes

Reaction equation

HRID 1583248 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:11]=O.[H][H]>C(O)C.[Pt]=O>[CH3:11][NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 227Anthranilic AcidHCID 712FormaldehydeHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67069N-Methylanthranilic acid

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A solution of 2-aminobenzoic acid (25 g) in ethanol (300 ml) reacted with an excess of paraformaldehyde and then reduced with hydrogen gas at 60 psi over platinum oxide (25 g) catalyst. After hydrogen uptake ceased, the mixture was filtered and the solvent removed on a rotary evaporator. The product was purified by chromatography on silica gel and the structure confirmed by nmr and infrared analysis.

Workup

  1. filtrationthe mixture was filtered
  2. customthe solvent removed on a rotary evaporator
  3. customThe product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ed246f2e1c7046a1a8e4929d902ad398
Source dataset
uspto-grants-1985_11
Patent number
US04551279

Reaction notes

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