2-(dimethylamino)-5-nitrobenzoic acid → 5-Amino-2-(dimethylamino)benzoic acid

HRID 450074Notes

Reaction equation

HRID 450074 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]>CO.[Pd]>[NH2:12][C:9]1[CH:10]=[CH:11][C:3]([N:2]([CH3:15])[CH3:1])=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 28046762-(dimethylamino)-5-nitrobenzoic acid

Product 1

HCID 28046925-Amino-2-(dimethylamino)benzoic acidYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-dimethylamino-5-nitro-benzoic acid (200 mg, 0.95 mmol) in methanol (15 ml) was hydrogenated over 10% Pd/C (20 mg) at 30 psi until no further gas uptake was observed. The reaction mixture was then filtered over celite and the filtrate evaporated to yield the crude product. Recrystallisation using pet. ether yielded 5-amino-2-dimethylamino-benzoic acid (110 mg, 70%).

Workup

  1. filtrationThe reaction mixture was then filtered over celite
  2. customthe filtrate evaporated
  3. customto yield the crude product
  4. customRecrystallisation

Sources & evidence

ORD record
ord-a441818196224a2daedc7bc7b87856e2
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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