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

HRID 1350928Notes

Reaction equation

HRID 1350928 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-a13fafeda6634dcb97bd88f334bfad72
Source dataset
uspto-grants-2007_05
Patent number
US07214715B2

Reaction notes

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