Ethanol → Methyl 3-amino-5-[(dipropylamino)carbonyl]Benzoate

HRID 852563

Reaction equation

HRID 852563 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[C:6]([C:7]([N:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.CCO>[Pd].O>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:18]=[C:17]([NH2:19])[CH:16]=[C:6]([C:7]([N:9]([CH2:10][CH2:11][CH3:12])[CH2:13][CH2:14][CH3:15])=[O:8])[CH:5]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 690570Methyl 3-[(dipropylamino)carbonyl]-5-nitrobenzoate

Product 1

HCID 22593627Methyl 3-amino-5-[(dipropylamino)carbonyl]BenzoateYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-nitro-N,N-dipropyl-isophthalamic acid methyl ester (D87) (1.5 g, 4.9 mmol, 1 equiv), NH4COOH (3.0 g, 49 mmol, 10 equiv), 10% Pd on charcoal (50% wet, 250 mg, 0.082 equiv w/w), EtOH (20 ml) and H2O (10 ml) was heated at 50° C. for 90 min. The mixture was cooled to room temperature, filtered through a pad of celite and concentrated in vacuo. The residue was dissolved in AcOEt (200 ml) and the resulting solution was washed with saturated NaHCO3 solution (100 ml), dried over MgSO4 and concentrated in vacuo to give 5-amino-N,N-dipropyl-isophthalamic acid methyl ester (D88) (1.2 g, 88%) as a white waxy solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in AcOEt (200 ml)
  5. washthe resulting solution was washed with saturated NaHCO3 solution (100 ml)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82322feba5904310bcdc5ebb0194cf1a
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Linked notes

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