Hydrochloric Acid → 4-Aminomethylisophthalic acid

HRID 33739Notes

Reaction equation

HRID 33739 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[C:12]([OH:14])=[O:13])#[N:2].Cl>[Pd].C(O)C>[NH2:2][CH2:1][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[C:12]([OH:14])=[O:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 226444314-Cyanoisophthalic acid

Product 1

HCID 226444344-Aminomethylisophthalic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A pressure flask was charged with 4-cyanoisophthalic acid 204 (1.40 g, 7.33 mmol), ethanol (100 mL), Pd/C (10%) (0.50 mg), and concentrated HCl (1.5 mL). The mixture solution was hydrogenated at 50 PSI overnight. The solid impurities were removed by filtration. Removal of solvent gave quantitative yield of 4-aminomethylisophthalic acid 205: 1H NMR (400 MHz, CD3OD) δ 4.46 (s, 2H), 7.69 (d, J=8 Hz, 1H), 8.26 (dd, J=2 Hz, J=8 Hz, 1H), 8.76 (d, J=1.7 Hz, 1H).

Workup

  1. customwas hydrogenated at 50 PSI overnight
  2. customThe solid impurities were removed by filtration
  3. customRemoval of solvent

Sources & evidence

ORD record
ord-ea8137a1574d43a7a6b7f63666d481de
Source dataset
uspto-grants-2008_09
Patent number
US07429651B2

Reaction notes

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