5-Methoxy-2-nitrobenzoic acid → 5-Methoxyanthranilic acid

HRID 1672324Notes

Reaction equation

HRID 1672324 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-])=O)=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9]>C(O)C.[Pd]>[NH2:12][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 1

HCID 3392095-Methoxy-2-nitrobenzoic acid

Product 1

HCID 2779305-Methoxyanthranilic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

17 g (86 mmol) of 5-methoxy-2-nitro-benzoic acid (Example 44c) in 170 ml ethanol are hydrogenated (1.013 bar) over 0.85 g Pd—C 10% for 8 h at ambient temperature. The catalyst is filtered off and ca. 50 ml 1N HCl are added. By evaporating the solvent, crystals start to precipitate. Crystallization is done from ethanol-diethyl ether. The compound is collected by filtration and dried at 50° C. (high vacuum). mp: 143-148° C.; MS: 166 (M+−1); HPLC: tret=7.42 min (Grad 3).

Workup

  1. customfor 8 h
  2. customat ambient temperature
  3. filtrationThe catalyst is filtered off
  4. additionca. 50 ml 1N HCl are added
  5. customBy evaporating the solvent, crystals
  6. customto precipitate
  7. customCrystallization
  8. filtrationThe compound is collected by filtration
  9. customdried at 50° C. (high vacuum)
  10. customtret=7.42 min (Grad 3)

Sources & evidence

ORD record
ord-ded5ccbe3442485c9d4cc5109c5cffb7
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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