3-Nitrophthalic acid → 3-Aminophthalic acid

HRID 1442849Notes

Reaction equation

HRID 1442849 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 vacua to a constant weight, affording 54 g (84% yield) of 3-aminopthalic 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 (brs, 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 vacua to a constant weight

Sources & evidence

ORD record
ord-c2277491be9447cf9dcd8b67d228e998
Source dataset
uspto-grants-2010_02
Patent number
US07659302B2

Reaction notes

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