2-Nitrobenzoic acid → Anthranilic Acid

HRID 632713Notes

Reaction equation

HRID 632713 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

HCID 110872-Nitrobenzoic acid

Product 1

HCID 227Anthranilic Acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% (wt.) Pd on activated carbon (0.05 equiv) was added to a flask charged with 2-nitrobenzoic acid (35) (1.0 equiv) under a N2 atmosphere. To the flask was added MeOH (0.25 M), and stirred under two H2 balloons overnight. After reaction complete, the flask was flushed with N2 gas, and the reaction mixture was filtered through celite. The volatiles were removed to afford crude 2-amino benzoic acid (36).

Workup

  1. customAfter reaction complete
  2. customthe flask was flushed with N2 gas
  3. filtrationthe reaction mixture was filtered through celite
  4. customThe volatiles were removed

Sources & evidence

ORD record
ord-247797745f1d46ae969aa6e6c03a8354
Source dataset
uspto-grants-2016_04
Patent number
US09321762B2

Reaction notes

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