Ethanol → 5-Amino-2-methylbenzoic acid

HRID 453365Notes

Reaction equation

HRID 453365 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CCO>CCOC(C)=O.[Pd]>[NH2:11][C:8]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 702EthanolHCID 5196832-Methyl-5-nitrobenzoic acid

Product 1

HCID 103746145-Amino-2-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a 250 mL round-bottomed flask was added 2-methyl-5-nitrobenzoic acid (5.0 g, 28 mmol) and palladium 10% on carbon (1.5 g, 14 mmol). The mixture was taken up in EtOAc (30 mL) then EtOH (70 mL) was added. The mixture was purged with H2 then allowed to stir at 1 atm. H2 for 24 h. LCMS indicated about 10% conversion to product. About 0.5 g 10% Pd/C and ˜30 mL MeOH was added to the reaction. The reaction was purged with H2 and let to stir at 1 atm H2 for 20 h. They reaction was monitored for complete conversion by LCMS. The mixture was passed through a pad of celite, washing with MeOH and concentrated to afford 5-amino-2-methylbenzoic acid as an off-white solid MS m/z found 152.1 (ESI, neg. ion).

Workup

  1. customThe mixture was purged with H2
  2. additionAbout 0.5 g 10% Pd/C and ˜30 mL MeOH was added to the reaction
  3. customThe reaction was purged with H2
  4. stirringto stir at 1 atm H2 for 20 h
  5. customThey reaction
  6. washwashing with MeOH
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-39d0f5bf6f354b27bbca42180e9a14b1
Source dataset
uspto-grants-2013_07
Patent number
US08492404B2

Reaction notes

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