4-(1-Ethyl-propylamino)-3-nitro-benzoic acid methyl ester → Methyl 3-amino-4-(pentan-3-ylamino)benzoate

HRID 1750188Notes

Reaction equation

HRID 1750188 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[C:6]([N+:16]([O-])=O)[CH:5]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[C:6]([NH2:16])[CH:5]=1

Participants

4

Reactant 1

HCID 859985714-(1-Ethyl-propylamino)-3-nitro-benzoic acid methyl ester

Product 1

HCID 61311526Methyl 3-amino-4-(pentan-3-ylamino)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7.00 g of 4-(1-Ethyl-propylamino)-3-nitro-benzoic acid methyl ester were dissolved in 70 ml ethanol, 0.35 g of palladium on carbon (10%) were added and the mixture was hydrogenated at 5 bar for 4 h. The catalyst was removed by filtration over celite, the filtrate was concentrated and after crystallization from diethylether 5.00 g (65%) of 3-Amino-4-(1-ethyl-propylamino)-benzoic acid methyl ester were obtained.

Workup

  1. customThe catalyst was removed by filtration over celite
  2. concentrationthe filtrate was concentrated
  3. customafter crystallization from diethylether 5.00 g (65%) of 3-Amino-4-(1-ethyl-propylamino)-benzoic acid methyl ester
  4. customwere obtained

Sources & evidence

ORD record
ord-56c220aef3724603bce099bbb4fd0797
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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