Methyl 4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)-3-nitrobenzoate → Methyl 3-amino-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)benzoate

HRID 1727414Notes

Reaction equation

HRID 1727414 reaction equation
[CH3:1][N:2]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=1[N+:17]([O-])=O>[Pd].C(OCC)(=O)C.CO>[NH2:17][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:7]=1[NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 1

HCID 69028187Methyl 4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)-3-nitrobenzoate

Product 1

HCID 69027376Methyl 3-amino-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

Methyl 4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)-3-nitrobenzoate (9.1 g) in solution in an ethyl acetate/methanol mixture and 10% palladium on carbon (910 mg) are added together in an autoclave. After stirring for 4 hours under a hydrogen atmosphere (3 bars), the catalyst is eliminated by filtration on Celite and the filtrate is concentrated under reduced pressure at 40° C. in order to produce the expected compound in the form of an oil (8.2 g, 98% yield).

Workup

  1. filtrationthe catalyst is eliminated by filtration on Celite
  2. concentrationthe filtrate is concentrated under reduced pressure at 40° C. in order

Sources & evidence

ORD record
ord-4bdca2e5a52745f9aabf8b131c46a284
Source dataset
uspto-grants-2009_02
Patent number
US07495110B2

Reaction notes

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