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

HRID 13999

Reaction equation

HRID 13999 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-613a07da640c446ead0bd7d29d250da4
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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