3-Nitrophthalic acid → 3-Aminophthalic acid

HRID 55749

Reaction equation

HRID 55749 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]=1[C:13]([OH:15])=[O:14])([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]=1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 2

HCID 690433-Nitrophthalic acidHCID 178418361HCID 178418361, compound3×

Product 1

HCID 794903-Aminophthalic acidYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C (2.5 g), 3-nitrophthalic acid (75.0 g, 355 mmol) and ethanol (1.5 L) were charged to a 2.5 L Parr hydrogenator under a nitrogen atmosphere. Hydrogen was charged to the reaction vessel for up to 55 psi. The mixture was shaken for 13 hours, maintaining hydrogen pressure between 50 and 55 psi. Hydrogen was released and the mixture was purged with nitrogen 3 times. The suspension was filtered through a celite bed and rinsed with methanol. The filtrate was concentrated in vacuo. The resulting solid was reslurried in ether and isolated by vacuum filtration. The solid was dried in vacuo to a constant weight, affording 54 g (84% yield) of 3-aminophthalic acid as a yellow product. 1H-NMR (DMSO-d6) δ: 3.17 (s, 2H), 6.67 (d, 1H), 6.82 (d, 1H), 7.17 (t, 1H), 8-10 (br, s, 2H); 13C-NMR (DMSO-d6) δ: 112.00, 115.32, 118.20, 131.28, 135.86, 148.82, 169.15, 170.09.

Workup

  1. customthe mixture was purged with nitrogen 3 times
  2. filtrationThe suspension was filtered through a celite bed
  3. washrinsed with methanol
  4. concentrationThe filtrate was concentrated in vacuo
  5. customisolated by vacuum filtration
  6. customThe solid was dried in vacuo to a constant weight

Sources & evidence

ORD record
ord-aac163278d774f779aaceb5fc6c049d3
Source dataset
uspto-grants-2016_09
Patent number
US09433606B2

Linked notes

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