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

HRID 1783188Notes

Reaction equation

HRID 1783188 reaction equation
[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([N+:17]([O-])=O)[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:6])[CH2:2][CH3:3]>[Pd].CO>[NH2:17][C:15]1[CH:14]=[C:9]([CH:8]=[C:7]([C:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:20][CH2:21][CH3:22])=[O:6])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 1

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

Product 1

HCID 22593627Methyl 3-amino-5-[(dipropylamino)carbonyl]Benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of methyl 3-[(dipropylamino)carbonyl]-5-nitrobenzoate (XXX, PREPARATION 9, 6.00g, 20.0 mmol) and palladium on carbon (5%, 0.600 g) in methanol (40 mL) is shaken in a hydrogenation apparatus under hydrogen (45 psi) for 3 hours. The mixture is then filtered through diatomaceous earth and concentrated to give the title compound, NMR (300 MHz, CDCl3) delta 7.27, 6.77, 4.10, 3.82, 3.38, 3.10, 1.62, 1.46, 0.91 and 0.68.

Workup

  1. filtrationThe mixture is then filtered through diatomaceous earth
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9ad4aa36b19048e5bdc7ad490731e929
Source dataset
uspto-grants-2009_03
Patent number
US07498436B2

Reaction notes

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